Home Cart Sign in  
Chemical Structure| 10272-49-8 Chemical Structure| 10272-49-8

Structure of 10272-49-8

Chemical Structure| 10272-49-8

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 10272-49-8 ]

CAS No. :10272-49-8
Formula : C11H16ClN
M.W : 197.70
SMILES Code : [H]Cl.C1(C2=CC=CC=C2)CCNCC1
MDL No. :MFCD01632527
InChI Key :UPZJLQCUYUTZIE-UHFFFAOYSA-N
Pubchem ID :82509

Safety of [ 10272-49-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 10272-49-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.45
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 62.2
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

12.03 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.19
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.57
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.67
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.8
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.25

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.35
Solubility 0.0881 mg/ml ; 0.000446 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.11
Solubility 0.152 mg/ml ; 0.000769 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.6
Solubility 0.0502 mg/ml ; 0.000254 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.24 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.01

Application In Synthesis of [ 10272-49-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 10272-49-8 ]

[ 10272-49-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 50-00-0 ]
  • [ 10272-49-8 ]
  • [ 774-52-7 ]
  • [ 98817-20-0 ]
  • 2
  • [ 13999-27-4 ]
  • [ 10272-49-8 ]
  • [ 14769-59-6 ]
  • 3
  • [ 50-00-0 ]
  • [ 41177-66-6 ]
  • [ 10272-49-8 ]
  • [ 96402-15-2 ]
  • 4
  • [ 50-00-0 ]
  • [ 484-27-5 ]
  • [ 10272-49-8 ]
  • [ 110469-35-7 ]
  • 5
  • [ 94163-98-1 ]
  • [ 10272-49-8 ]
YieldReaction ConditionsOperation in experiment
97% With palladium 10% on activated carbon; hydrogen; In ethanol; for 44h; General procedure: The starting material (either 1-benzyl-4-aryl-1,2,3,6-tetrahydropyridine, its hydrochloride salt; or 4-aryl-1,2,3,6-tetrahydropyridinium chloride) (1 mmol) was dissolved in the specified alcohol (10 mL) and stirred vigorously under an atmosphere of hydrogen in the presence of 10% palladium on carbon (0.1 molar equivalents). The progress of the reaction was monitored by TLC (10% methanol / chloroform with 1% ammonia) every 12 h and, if incomplete, additional palladium on carbon (0.01 molar equivalents) was added. When the starting material had been completely consumed (TLC, Rf usually 0.75-0.95 for the 1-benzyl compounds, Rf usually 0.15-0.25 for the tetrahydropyridines) and the presence of the desired product was evident (TLC, Rf usually 0.1-0.2) the reaction was worked up by filtration through Celite followed by rinsing with the alcohol used (2 × 5 mL) and removing all solvent in vacuo to give the title compound as a solid. If the final product was deemed pure enough for initial biological evaluation (>95% by HPLC), it was dried under vacuum in the presence of phosphorous pentoxide. If the final product was not sufficiently pure enough for initial testing (<95% by HPLC), it was either recrystallized or subject to preparative HPLC as described in the specific procedure below.
  • 6
  • [ 3351-59-5 ]
  • [ 10272-49-8 ]
  • 1-<2-(4-benzyloxyphenyl)ethoxy>-4-phenylpiperidine [ No CAS ]
  • 7
  • [ 10272-49-8 ]
  • [ 201609-25-8 ]
  • 2a-[4-(4-phenylpiperidyl)butyl]-2a,3,4.5-tetrahydrobenz[cd]indole-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% This compound was synthesized in the same manner as described in Example 5, except that <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (Example 4) was used in stead of 4-(2-methoxyphenyl)piperazine (yield, 91%). 1H-NMR (CDCl3) delta 1.02-1.14 (1 H, m), 1.22-1.54 (4 H, m), 1.75-1.93 (7 H, m), 2.07-2.20 (2 H, m), 2.23-2.36 (2 H, m), 2.41-2.51 (1 H, m), 2.60-2.70 (1 H, m), 2.80-2.90 (1 H, m), 2.95-3.04 (2 H, m), 6.67 (1 H, d, J=7.8 Hz), 6.81 (1 H, d, J=7.8 Hz), 7.12 (1 H, dd), 7.26-7.24 (3 H, m), 7.25-7.33 (3 H, m); MW 388.55 (C26H32N2O); Mass spectrum LC m/z 389 (M+H)+ The thus obtained free compound was dissolved in hydrochloric acid-saturated methanol to obtain its hydrochloric acid salt. MW 425.01 (C26H33ClN2O); Mass spectrum LC m/z 389 (M-HCl+H)+
  • 8
  • [ 10272-49-8 ]
  • [ 304858-54-6 ]
  • 1-methyl-5-oxo-N-phenyl-N-[3-(4-phenylpiperidin-1-yl)propyl]pyrrolidine-3-carboxamide [ No CAS ]
  • 9
  • [ 10272-49-8 ]
  • methyl 3-(4-methanesulfonyloxybutyl)-1H-indole-5-carboxylate [ No CAS ]
  • 3-[4-(4-phenyl-piperidin-1-yl)-butyl]-1<i>H</i>-indole-5-carboxylic acid methyl ester [ No CAS ]
  • 10
  • [ 10272-49-8 ]
  • methanesulfonic acid 4-(5-carbamoyl-1<i>H</i>-indol-3-yl)-butyl ester [ No CAS ]
  • 3-[4-(4-phenyl-piperidin-1-yl)-butyl]-1<i>H</i>-indole-5-carboxylic acid amide [ No CAS ]
  • 11
  • [ 50-00-0 ]
  • [ 10272-49-8 ]
  • [ 829-33-4 ]
YieldReaction ConditionsOperation in experiment
77% Example 10: (E)-N-Hydroxy-3-(4-{(E)-3-[4-(1-methyl-piperidin-4-yI)-phenyl]-3- oxo-propenyl}-phenyl)-acrylamde; STEP A; A mixture of 4-phenyl piperidine hydrochloride (1.23 g, 6.2 mmol), formaldehyde (36.5% in H2O, 0.702 ml, 9.3 mmol), NaBH(OAc)3 (2.63 g, 12.42 mmol) and AcOH (0.71 ml, 12.42 mmol) in DCM (30 ml) was stirred for 24 hours at room temperature. The mixture was then brought to basic conditions with a 5% NaHCO3 solution and extracted twice with DCM. The pooled organic phases were dried over Na2SO4 and evaporated to dryness. The residue was dissolved in DCM and treated with HCI in Et2O observing the precipitation of a white solid. The solid was filtered off through a Buchner funnel to obtain 1 g of 1-methyl-4- phenylpiperidine hydrochloride as a white solid. Y = 77%
  • 12
  • [ 1000771-62-9 ]
  • [ 10272-49-8 ]
  • 4-[2-(4-phenyl-piperidine-1-yl)-ethyl]-4H-benzo[1,4]oxazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With borane pyridine; In ethanol; Following the procedure of Synthetic Comm. 23 (6), 789-795, 1993, to a solution of <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> Compound 1-9 (290 mg, 1.5 mmol) and Compound 1-4 (300 mg, 1.5 mmol) in 10 mL of absolute ethanol was added BAP (154 muL, 1.5 mmol). After stirring for 2 hrs, an additional equivalent of aldehyde Compound 1-4 and BAP was added. The reaction mixture was stirred overnight and concentrated to give an oily residue. The residue was taken up in DCM, washed with saturated sodium bicarbonate solution NaHCO3 and brine, dried over Na2SO4, and concentrated. The residue was purified on silica gel (elution with 30% EtOAc in hexane) to yield Compound 86 as a glass-like oil (287 mg, 57%) of a glass-like oil. 1H NMR (300 MHz, CDCl3) delta 7.25-7.11 (m, 5H), 7.04-6.91 (m, 4H), 4.53 (s, 2H), 4.04 (m, 2H), 3.04 (m, 2H), 2.58 (m, 2H), 2.45-2.40 (m, 1H), 2.15, (t of d, J=11 and 3 Hz, 2H), 1.83-1.64 (m, 4H); MS (ES+) m/z 337.2 (M+1); Anal Calcd. for C21H24N2O2.0.51H2O: C, 73.02; H, 7.29; N, 8.11. Found: C, 72.98; H, 7.11; N, 8.00.
  • 13
  • [ 10272-49-8 ]
  • 3-[4-(4-phenyl-piperidin-1-yl)-butyl]-1<i>H</i>-indole-5-carboxylic acid [ No CAS ]
  • 14
  • [ 10272-49-8 ]
  • [ 14827-76-0 ]
  • 15
  • [ 10272-49-8 ]
  • [ 304858-54-6 ]
  • 1-methyl-5-oxo-N-phenyl-N-[3-(4-phenyl-1-piperidinyl)propyl]-3-pyrrolidinecarboxamide fumarate [ No CAS ]
  • 16
  • [ 43064-12-6 ]
  • [ 10272-49-8 ]
YieldReaction ConditionsOperation in experiment
99% carbon palladium; In methanol; Reference Example 8 4-Phenylpiperidine Hydrochloride 1,2,3,6-Tetrahydro-4-phenylpyridine hydrochloride (70 mg) was dissolved in methanol (1.4 ml), added with 10% palladium/carbon (35 mg) and stirred at 45 C. for 5 hours under hydrogen gas atmosphere. After insoluble matters were removed by filtration, the solvent was evaporated under reduced pressure to obtain 70.0 mg of the title compound. Yield: 99%. 1H-NMR(CD3OD) delta (ppm); 1.93 (2H, m), 2.06 (2H, m), 2.89 (1H, m), 3.13 (2H, m), 3.49 (2H, m), 7.20-7.34 (5H, m) MS (EI); m/z 161 (M+)
99% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 4h;Inert atmosphere; To a stirred solution of 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride (300 mg, 1.53mmol) in MeOH (10 mL), 10% Pd-C (100 mg) was added at RT under argon atmosphere.The reaction mixture was flushed with H2 (3 times) and stirred under H2 atmosphere (balloon)for 4 h. After completion of the reaction (monitored by LCMS), the reaction mixture wasfiltered through a short pad of Celite and washed with MeOH (5 mL). The filtrate wasconcentrated under reduced pressure and the residue was washed with dry ether (2 x 5 mL) togive 4-phenylpiperidine hydrochloride (300 mg, 99%) as an off-white solid (hygroscopic).LCMS: m/z: 162.3 [M+Ht.
97% With hydrogen;5%-palladium/activated carbon; In methanol; under 1551.49 Torr; for 1h; 4-(4-Nitrophenyl)piperidine 4-Phenyl-1,2,3,6-tetrahydropyridine hydrochloride (10.38 g; 53.0 mmol) dissolved in methanol (160 ml) in the presence of palladium-on-charcoal (5%) (1.04 g) is hydrogenated under 30 psi of hydrogen for 1 hour.The medium is filtered through Celite and the filtrate is evaporated to dryness to give 4-phenylpiperidine hydrochloride (10.17 g; 97%).This intermediate (13 g; 65.7 mmol) is taken up in chloroform (430 ml), cooled to 0 C. and then treated with copper nitrate 2.5-hydrate (15.3 g; 65.7 mmol) for 15 minutes.The mixture is then added dropwise over 45 minutes to a solution of trifluoroacetic anhydride (65 ml; 460 mmol) in chloroform (70 ml).After stirring at 0 C. for 48 hours, the medium is poured onto ice, diluted with dichloromethane and neutralized by addition of concentrated sodium hydroxide (85 ml).The medium is extracted several times with dichloromethane and the organic phases are then combined, dried over magnesium sulfate, filtered and evaporated to dryness.The syrup obtained is purified by chromatography on a column of silica eluted with a 96.5/3/0.5 CH2Cl2/MeOH/NH4OH mixture to give pure compound 141A (8.35 g; 68%).
93% With hydrogen;10% palladium on activated carbon; In methanol; for 19h; 1,2,3,6-Tetrahydro-4-phenylpyridine hydrochloride (200 mg, 1.0 mmol) and 10% palladium-carbon (30 mg) were stirred in methanol (2 ml) for 19 hours in an atmosphere of hydrogen. The reaction solution was filtered and the resulting residue was thoroughly washed with methanol. Then the filtrate and washed solution were combined and evaporated under a reduced pressure to obtain 190 mg of the title compound (0.95 mmol, 93% in yield). 1H-NMR (CDCl3) delta 2.01-2.10 (2 H, m), 2.17-2.30 (2 H, m), 2.72-2.82 (1 H, m), 2.98-3.07 (2 H, m), 3.60-3.68 (2 H, m), 7.22-7.29 (3H, m), 7.31-7.37 (2 H, m); MW 197.71 (C11H16ClN); Mass spectrum EIMS m/z 161 (M)+
palladium; In methanol; ethyl acetate; Reference Example 4 4-Phenylpiperidine hydrochloride 1,2,5,6-Tetrahydro-4-phenylpyridine hydrochloride (125 g) and 12.0 g of 10 % palladium on carbon were suspended in 1 L of methanol, and the suspension was stirred at atmospheric pressure under a hydrogen atmosphere at room temperature for 5 hours. The insoluble material was removed through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was suspended in ethyl acetate and a small amount of ethanol, and the insoluble material was collected by filtration to give 60.3 g of 4-phenylpiperidine hydrochloride. 1H-NMR(DMSO-d6) delta ppm: 1.79-2.01 (4H, m), 2.73-3.08 (3H, m), 3.20-3.45 (2H, m), 7.10-7.40 (5H, m), 9.18 (2H, br-s)

  • 17
  • [ 10272-49-8 ]
  • [ 26905-03-3 ]
YieldReaction ConditionsOperation in experiment
68% 4-Phenyl-1,2,3,6-tetrahydropyridine hydrochloride (10.38 g; 53.0 mmol) dissolved in methanol (160 ml) in the presence of palladium-on-charcoal (5%) (1.04 g) is hydrogenated under 30 psi of hydrogen for 1 hour.The medium is filtered through Celite and the filtrate is evaporated to dryness to give <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (10.17 g; 97%).This intermediate (13 g; 65.7 mmol) is taken up in chloroform (430 ml), cooled to 0 C. and then treated with copper nitrate 2.5-hydrate (15.3 g; 65.7 mmol) for 15 minutes.The mixture is then added dropwise over 45 minutes to a solution of trifluoroacetic anhydride (65 ml; 460 mmol) in chloroform (70 ml).After stirring at 0 C. for 48 hours, the medium is poured onto ice, diluted with dichloromethane and neutralized by addition of concentrated sodium hydroxide (85 ml).The medium is extracted several times with dichloromethane and the organic phases are then combined, dried over magnesium sulfate, filtered and evaporated to dryness.The syrup obtained is purified by chromatography on a column of silica eluted with a 96.5/3/0.5 CH2Cl2/MeOH/NH4OH mixture to give pure compound 141A (8.35 g; 68%). 1H NMR, d6-DMSO (ppm): 1.52 m, 2H; 2.59 t, 2H; 2.75 dt, 1H; 3.19 broad s, 2H; 7.52 d, 2H; 8.16 d, 2H;
4-Phenylpiperidine hydrochloride (3 g, 15 mmol) was dissolved in concentrated sulfuric acid (3 g), followed by dropwise addition of concentrated nitric acid at 0C. The solution was slowly warmed to rt and left at this temperature for 1 day. The mixture was poured into ice water and treated with 1N NAOH until basic. The solution was then extracted by ethyl ether. The extracts were combined, dried over MGS04, and evaporated. The residue was recrystalized in ethyl ether to provide pure product (1.5 g). LC-MS M+H 207.
  • 18
  • [ 214770-65-7 ]
  • [ 74124-79-1 ]
  • [ 10272-49-8 ]
  • methyl (2R,3S)-3-(1H-indol-3-yl)-2-[((4-phenyl-piperidine)carbonyl)-amino]butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 20℃; for 17h; To a solution of methyl (2R, 3S)-2-AMINO-3- (LH-INDOL-3- yl) butanoate (325 mg) and diisopropylethylamine (0.293 mL) in acetonitrile (10 mL) was added N, N'-DISUCCINIMIDYL carbonate (390 mg) under ice-cooling and the mixture was stirred for 1 hour. To the obtained solution was added a solution of 4- phenylpiperidine hydrochloride (332 mg) and DBU (0.252 mL) in acetonitrile (1 mL) and diisopropylethylamine (0.293 mL) under ice-cooling. The reaction solution was stirred at room temperature for 16 hours, and a saturated aqueous solution of sodium hydrogen carbonate was added. The mixture was extracted with ethyl acetate. The extract was purified by silica gel column chromatography (developing solvent ; ethyl acetate) to give the title compound as a colorless amorphous powder (0.66 g, yield 100%). 1H NMR (300 MHz, CDC13) 8 ppm : 1.50 (d, J = 7.3 Hz, 3 H), 1.54 - 1. 69 (m, 2 H), 1.77-1. 81 (m, 2 H), 2.57-2. 67 (m, 1 H), 2.73-2. 88 (m, 2 H), 3.62 (s, 3 H), 3.64-3. 71 (m, 1 H), 3.89-3. 95 (m, 1 H), 4.01-4. 08 (m, 1 H), 4.83 (dd, J = 8.1, 5.4 Hz, 1 H), 5. 01 (d, J = 8.8 Hz, 1 H), 7.02 (d, J = 2.4 Hz, 1 H), 7.07-7. 22 (m, 5 H), 7. 27-7. 36 (m, 3 H), 7.62 (d, J = 7.3 Hz, 1 H), 8.14 (s, 1 H).
  • 19
  • [ 697304-66-8 ]
  • [ 74124-79-1 ]
  • [ 10272-49-8 ]
  • [ 697304-21-5 ]
YieldReaction ConditionsOperation in experiment
93% With 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 20℃; for 17h; A mixture of ethyl (2R, 3S)-2-AMINO-3- (LH-INDOL-3- YL) BUTANOATE O, O'-DIACETYL-L-TARTARATE (7.21 g) and a saturated aqueous solution of sodium hydrogen carbonate (35 mL) -ethyl acetate (40 mL) was stirred at room temperature for 2 hrs. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was dried (MGSO4) and the solvent was evaporated to give ethyl (2R, 3S)-2-AMINO-3-(LH-INDOL-3-YL) butanoate as a colorless oil (3.69 G, yield 100%). To a solution of the obtained oil (2.22 g) and N, N- diisopropylethylamine (1.98 mL) in acetonitrile (60 mL) was added N, N'-DISUCCINIMIDYL carbonate (2.65 g) under ice-cooling, and the mixture was stirred for 1 hr. To the obtained solution was added a solution of <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (2.25 g) and DBU (1.71 mL) in acetonitrile (10 mL) and N, N- diisopropylethylamine (1.98 mL) was added under ice-cooling. The reaction solution was stirred at room temperature for 16 hrs. and a saturated solution of sodium hydrogen carbonate was added. The mixture was extracted with ethyl acetate and the extract was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate = 1/1-1/4) to give the title compound as a white amorphous powder (3.62 g, yield 93%). LC/MS (ESI) m/z 434 (M+H+).
  • 20
  • [ 54672-55-8 ]
  • [ 10272-49-8 ]
  • 2,3-dihydro-2-[(4-phenylpiperidin-1-yl)carbonyl]-1H-indene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; 750 mg (4.6 mmol) of 2,3-dihydro-1H-inden-2-carboxylic acid (prepared as described in Hacksell, J. Med. Chem., 24, 429, 1981) were dissolved in 15 mL of CH2Cl2 and 0.65 mL (7.4 mmol) of oxalyl chloride were added dropwise at 0 C. under a nitrogen atmosphere. The solution was allowed to warm to room temperature in 2 h, then the solvent was removed in vacuo. The resulting acyl chloride was dissolved in 10 mL of CH2Cl2 and added to a solution of 909 mg (4.6 mmol) of <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> and 1.9 mL (13.8 mmol) of triethylamine in 15 mL of CH2Cl2 at 0 C. The reaction mixture was allowed to warm to room temperature overnight, then water was added and the organic phase was washed with 5% HCl and dried. The solvent was removed in vacuo and the resulting crude product was purified by flash chromatography, eluting with a mixture Et2O/Petroleum ether 7:3, yielding 630 mg of the title compound. IR (cm-1)=2944, 1636, 1494. NMR (300 MHz, CDCl3, delta ppm): 7.35 (m, 2H); 7.25-7.1 (m, 7H); 4.85 (m, 1H); 4.15 (m, 1H); 3.55 (m, 1H); 3.4-3.3 (m, 2H); 3.3-3.1 (m, 3H); 2.85-2.6 (m, 2H); 2.0-1.9 (m, 2H); 1.75.1.6 (m, 2H). MS (m/z): 306.0 (MH+).
  • 21
  • [ 24566-79-8 ]
  • [ 10272-49-8 ]
  • [ 387827-41-0 ]
YieldReaction ConditionsOperation in experiment
77% With ammonia; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; chloroform; 2-[6-(4-phenyl-1-piperidinyl)hexyl]-1H-isoindole-1,3(2H)-dione: To the 500 ml RB-flask was added <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (5 g, 25 mmol), N-(6-bromohexyl)phthalimide (15.5 g, 50 mmol), N,N-diisopropylethylamine (21.8 ml, 125 mmol), tetrabutylammonium iodide (0.2 g), and dioxane (250 ml) at room temperature. The reaction mixture was stirred at 100 oC for 72 h. The solvent was removed in vacuo and the crude product was purified by flash chromatography (98:2=Chloroform: 2N ammonia in methanol) to afford 7.67 g of the desired product (77% yield): 1H NMR (400 MHz, CDCl3) delta 7.78-7.79 (m, 2H), 7.74-7.65 (m, 2H), 7.32-7.14 (m, 5H), 3.69 (t, 2H, J=7.35 Hz), 3.06 (d, 2H, J=11.0 Hz), 2.49 (quintet, 1H, J=7.6 Hz), 2.36 (t, 2H, J=7.6 Hz), 2.02 (t, 2H, J=12.5 Hz), 1.82 (br s, 4H), 1.69 (t, 2H, J=6.3 Hz), 1.54 (br s, 2H), 1.37 (br s, 4H); ESMS m/e: 391.3 (M+H) +; Anal. Calc. for C25H30N2O2+0.2H2O: C, 76.19; H, 7.77; N, 7.11. Found: C, 76.14; H, 7.38; N, 7.13.
77% With ammonia; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; chloroform; 2-[6-(4-PHENYL-1-PIPERIDINYL)HEXYL]-1H-ISOINDOLE-1,3(2H)-DIONE: To the 500 ml RB-flask was added <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (5 g, 25 mmol), N-(6-bromohexyl)phthalimide (15.5 g, 50 mmol), N,N-diisopropylethylamine (21.8 ml, 125 mmol), tetrabutylammonium iodide (0.2 g), and dioxane (250 ml) at room temperature. The reaction mixture was stirred at 100 C. for 72 h. The solvent was removed in vacuo and the crude product was purified by flash chromatography (98:2=Chloroform: 2N ammonia in methanol) to afford 7.67 g of the desired product (77% yield): 1H NMR (400 MHz, CDCl3) delta 7.78-7.79 (m, 2H), 7.74-7.65 (m, 2H), 7.32-7.14 (m, 5H), 3.69 (t, 2H, J=7.35 Hz), 3.06 (d, 2H, J=11.0 Hz), 2.49 (quintet, 1H, J=7.6 Hz), 2.36 (t, 2H, J=7.6 Hz), 2.02 (t, 2H, J=12.5 Hz), 1.82 (br s, 4H), 1.69 (t, 2H, J=6.3 Hz), 1.54 (br s, 2H), 1.37 (br s, 4H); ESMS m/e: 391.3 (M+H)+; Anal. Calc. for C25H30N2O2+0.2H2O: C, 76.19; H, 7.77; N, 7.11. Found: C, 76.14; H, 7.38; N, 7.13.
77% With N-ethyl-N,N-diisopropylamine;tetra-(n-butyl)ammonium iodide; In 1,4-dioxane; at 100℃; for 72h; To the 500 ml RB-flask was added <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (5 g, 25 mmol), N-(6-bromohexyl)phthalimide (15.5 g, 50 mmol), N,N-diisopropylethylamine (21.8 ml, 125 mmol), tetrabutylammonium iodide (0.2 g), and dioxane (250 ml) at room temperature. The reaction mixture was stirred at 100 C. for 72 h. The solvent was removed in vacuo and the crude product was purified by flash chromatography (98:2=Chloroform:2N ammonia in methanol) to afford 7.67 g of the desired product (77% yield): 1H NMR (400 MHz, CDCl3) delta 7.78-7.79 (m, 2H), 7.74-7.65 (m, 2H), 7.32-7.14 (m, 5H), 3.69 (t, 2H, J=7.35 Hz), 3.06 (d, 2H, J=11.0 Hz), 2.49 (quintet, 1H, J=7.6 Hz), 2.36 (t, 2H, J=7.6 Hz), 2.02 (t, 2H, J=12.5 Hz), 1.82 (br s, 4H), 1.69 (t, 2H, J=6.3 Hz), 1.54 (br s, 2H), 1.37 (br s, 4H); ESMS m/e: 391.3 (M+H)+; Anal. Calc. for C25H30N2O2+0.2H2O: C, 76.19; H, 7.77; N, 7.11. Found: C, 76.14; H, 7.38; N, 7.13.
  • 22
  • [ 691875-88-4 ]
  • [ 10272-49-8 ]
  • C30H30F6N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With sodium triacetoxyborohydride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20℃;Molecular sieve; A solution of Intermediate 12 (Intermediate 12,100. 0 mg, 0.256 mmol) 4- phenylpiperidine hydrochloride (70.0 mg, 0.354 mmol), diisopropylethylamine (62, UL, 0.354 mmol) and crushed molecular sieves (4A, 50 mg) in dichloroethane (5 ML) was treated with sodium triacetoxyborohydride (378 mg, 1.78 mmol) and stirred at room temperature overnight. The sieves were filtered off (plug of Celite), washed with dichloromethane and the combined organic washings were extracted with a saturated solution of sodium bicarbonate (1 x 10 ML), water (2 x 10 mL), brine (1 x 10 mL) and dried over anhydrous sodium sulfate. Solvent was evaporated to dryness to yield 120 mg (86 %) of the crude product. The residue was purified by preparative TLC (eluent: 5% methanol/95% ethyl acetate) to yield 84.6 mg (60 %) of the final pure desired product. LC-MS for C32H3ON2OF6 [M + H] + calculated 548.23, found 549.
  • 23
  • [ 139354-85-1 ]
  • [ 10272-49-8 ]
  • [ 691876-43-4 ]
YieldReaction ConditionsOperation in experiment
96% With sodium triacetoxyborohydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; A mixture of 3.42 g (10 mmol) of ethyl 2- (2-TERT- BUTOXYCARBONYLAMINOTHIAZOL-4-YL)-3-FORMYLPROPANOATE (Intermediate 36), 1.61 g (10 mmol) of phenylpiperidine hydrochloride, 2.6 g (20 mmol) of DIEA and 4.22 g (20 mmol) of sodium triacetoxyborohydride in 20 ML of CH2C12 at RT was stirred for 0.5 h. The reaction mixture was diluted with 50 ML of CH2C12 and washed with water (3x 100 ML). The organic phase was dried over NA2SO4 and concentrated in vacuo. 4.55 g (96%) of the title compound was obtained as a gummy material. 1H NMR (300 MHz, CDC13) : 8 1. 21 (t, 3H), 1.53 (s, 9H), 1.70-1. 90 (m, 4H), 1.95-2. 15 (m, 3H), 2.20-2. 55 (m, 4H), 3.00-3. 10 (m, 2H), 3.77 (t, 1H), 4.10-4. 20 (m, 2H), 6.69 (s, 1H), 7.18-7. 35 (m, 5H). Mass Spectrum (NH3-CI) : m/z 474 (M+1).
  • 24
  • [ 691877-08-4 ]
  • [ 10272-49-8 ]
  • [ 691877-09-5 ]
YieldReaction ConditionsOperation in experiment
With sodium triacetoxyborohydride; triethylamine; In dichloromethane; at 20℃; for 2h; The aldehyde intermediate from the preceding step (1.94 g, 6.65 mmol) was combined with triethylamine (1.11 ML, 807 mg, 7.98 mmol) and phenylpiperidine hydrochloride (1.58 g, 7.98 mmol) in DCM (40 mL). Then NaB (OAc) 3H (4.23 g, 20.0 mmol) was added and the reaction mixture was stirred at rt for 2 h. The reaction mixture was then diluted with DCM (200 mL), and washed sequentially with saturated NAHC03 solution, and brine, dried over MGS04, filtered and concentrated to give 2.93 g of crude product which was used without further purification. H NMR (CDC13, 500 MHz) : 8 7.16-7. 31 (m, 6H), 4.19 (m, 2H), 3.97 (t, J = 7.0 Hz, 1H), 3.06 (app dd, J = 25.5, 11.0 Hz, 2H), 2.43-2. 52 (m, 3H), 2.34 (m, 1H), 2.09-2. 17 (m, 3H), 1.83 (br s, 4H), 1.26 (t, J = 7. 0 HZ, 3H).
  • 25
  • [ 787640-50-0 ]
  • [ 10272-49-8 ]
  • C27H29F6N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h; To a mixture of the compound described in Step E (100 mg, 0.263 MMOL), 4-PHENYLPIPERIDINE HCI salt (52 mg, 0.26 mmol), molecular sieve (4 A, 180 mg), DIEA (46 ZL, 0.26 mmol) in DCM (5 mL), was added sodium triacetoxyborohydride (167 mg, 0.789 mmol) and the resulting mixture was stirred overnight at room temperature. The reaction was diluted with DCM, filtered through celite, and evaporated under reduced pressure. The residue was purified by preparative TLC (1000 micron, eluant : 0.4 % aqueous NH40H : 4 % MeOH : 95.6 % DCM) to yield a mixture of cis-and trans-isomers as a free base. The cis-and trans-isomers were separated by preparative chiral HPLC (chiral OD column, eluant : 5 % ETOH/HEXANE) to yield the final product of the title compound as the desired cis isomers. Its HCL salt (20.4 mg) was formed by treatment with 4 N HCL/DIOXANE. H-NMR (400MHZ, CDCI3) 6 8.74 (s, 1H), 7.70 (s, 1H), 7.20-7. 35 (m, 5H), 4.85 (m, 2H), 3.99 (m, 2H), 3.14-3. 24 (m, 5H), 2.46-2. 56 (m, 3H), 2.02-2. 22 (m, 5H), 1.70- 1.91 (m, 5H). LC-MS calc. for C27H29F6N30: 525.22 ; Found: 526 (M+H).
  • 26
  • [ 10272-49-8 ]
  • [ 374813-20-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In p-nitrophenyl(1,2,3,4-tetrahydroquinoline)carbamate; dimethyl sulfoxide; ethyl acetate; 2) 4-Nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylate obtained in 1) above was dissolved in DMSO (10 ml), and <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (1.58 g, 7.97 mmol) and 4 N aqueous sodium hydroxide (2.09 ml, 8.36 mmol) were added thereto and stirred at room temperature for 22.5 hours. 60 ml ethyl acetate was added to the reaction solution which was then washed with an aqueous potassium carbonate solution and a saturated saline solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure, and the resultant residues were purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=2:1), whereby 2.10 g of the title compound was obtained as pale yellow liquid. 1H-NMR (CDCl3) delta: 1.68 (2H, m), 1.80 (2H, m), 1.98 (2H, m), 2.65 (1H, m), 2.78 (2H, dd, J=6.6 and 6.9 Hz), 2.85 (2H, m), 3.62 (2H, t, J=6.1 Hz), 3.95 (2H, m), 6.90 (1H, m), 7.04-7.32 (8H, m).
  • 27
  • [ 10272-49-8 ]
  • [ 478178-91-5 ]
YieldReaction ConditionsOperation in experiment
N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; EXAMPLE 6 2-Methyl-5-nitro-6-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-3H-pyrimidin-4-one In analogy to the procedure described in example 1, the 6-bromo-2-methyl-5-nitro-3H-pyrimidin-4-one (prepared as in Eur. Pat. Appl. EP 1 074 549 A2) was treated with the 1,2,3,6-tetrahydro-<strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> in N,N-dimethylformamide in the presence of N-ethyldiisopropylamine at room temperature to yield the 2-methyl-5-nitro-6-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-3H-pyrimidin-4-one as yellowish solid; m.p. 212-216 C. (decomposition); MS: [M+H]+=313.
  • 28
  • [ 10272-49-8 ]
  • [ 400770-04-9 ]
YieldReaction ConditionsOperation in experiment
1.83 g (100%) With sodium tris(acetoxy)borohydride;silica gel; In 1,2-dichloro-ethane; Step A Methyl 3-(4-phenyl)piperidin-1-yl)-1-isopropylcyclopentane carboxylate To a solution of the methyl 3-oxo-1-isopropylcyclopentane carboxylate (see Intermediate 12, Step D, 1.0 g, 5.43 mmol), <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (1.074, 5.43 mmol), crushed 4 A molecular sieves (3.84 g) in anhydrous 1,2-dichloroethane (50 mL) and diisopropylethylarnine (946 muL, 5.43 mmol), was added sodium triacetoxyborohydride (3.45 g, 16.3 mmol). The mixture was stirred at room temperature for 48 hours, diluted with dichloromethane (50 mL), and filtered through celite. The filtrate was washed with saturated NaHCO3 solution (50 mL), water (50 mL), saturated NaCl (20 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 1.83 g (100%) of the desired product as a approximately 1:1 mixture of the respective cis- and trans- diastereoisomeric esters. This material was used in the next step without further purification. LC-MS for C21H32NO2 [M+H]+calculated 330.24, found 330.35.
YieldReaction ConditionsOperation in experiment
4-Phenyl piperidine HCl (B-3) A mixture of 4-hydroxy-4-phenylpiperidine (B-2) (39.7 g, 0.224 mol) and Pd/C (4.0 g) and concentrated HCl (20 mL) was subjected to hydrogenation H2 (50 psi) for 20 hours at 40 C. The solid was filtered through celite, and the filtrate was concentrated. A white solid was obtained by recrystallization from ethanol-ether (36.3 g, 82%), mp 170-173 C.
  • 30
  • [ 191475-11-3 ]
  • [ 10272-49-8 ]
  • 3-[4-(4-Phenyl-piperidin-1-yl)-benzenesulfonyl-amino]-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.082 g (21%) With sodium carbonate; In dichloromethane; dimethyl sulfoxide; (b) 3-[4-(4-Phenyl-piperidin-1-yl)-benzenesulfonylamino]-propionic acid A stirred mixture of 3-[4-fluoro-(benzenesulfonyl amino)]-propionic acid, sodium salt (0.248 g, 0.00100 mol), 4-phenyl-piperidine hydrochloride (0.218 g, 0.00110 mol), and sodium carbonate (0.317 g, 0.00299 mol) in dry dimethyl sulfoxide (3 mL) was heated in a sand bath (130 C.) under nitrogen for 22 hours. The mixture was cooled and partitioned between ethyl acetate and 1 M hydrochloric acid. The aqueous layer was extracted with additional ethyl acetate. The organics were combined, washed with saturated sodium chloride, dried (MgSO4), and rotary evaporated. The residue was dissolved in dichloromethane and chromatographed on silica gel (14 g, 230-400 mesh) eluding with dichloromethane-methanol (15:1, 10*15 mL). Fractions containing product were combined, rotary evaporated and rechromatographed to give the title compound as a peach-colored solid; yield 0.082 g (21%), mp=145-147 C.
  • 31
  • [ 10272-49-8 ]
  • [ 157133-89-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; trifluoroacetic anhydride; In diethyl ether; dichloromethane; Reference Example 5 4-Phenyl-1-trifluoroacetylpiperidine To 50 ml of dichloromethane were added 10.0 g of <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> and 25 ml of triethylamine, and 8.5 ml of trifluoroacetic anhydride was added dropwise to the mixture under ice-cooling. After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The resulting residue was suspended in diethyl ether, the insoluble material was removed through Celite, and the filtrate was washed successively with water, dilute hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 12.45 g of 4-phenyl-1-trifluoroacetylpiperidine. 1H-NMR(CDCl3) delta ppm: 1.63-1.80 (2H, m), 1.90-2.07 (2H, m), 2.74-2.93 (2H, m), 3.17-3.32 (1H, m), 4.06-4.21 (1H, m), 4.62-4.78 (1H, m), 7.11-7.40 (5H, m)
  • 32
  • [ 946493-50-1 ]
  • [ 10272-49-8 ]
  • 4-phenyl-1-(2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)ethyl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With potassium carbonate;sodium iodide; In N,N-dimethyl-formamide; at 110℃; A mixture of 4-(2-chloroethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene (0.25 g, 1.24 mmol), <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (0.25 g, 1.25 mmol), K2CO3 (0.40 g, 2.89 mmol) and a catalytic amount of Nal in DMF (5 mL) is heated to 110C overnight. The solvent is removed at reduced pressure, diethyl ether is added to the residue and washed with water. The organic phase is dried and evaporated at reduced pressure and the resulting crude is purified by column chromatography, giving 4-phenyl-1-(2-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)ethyl)piperidine (0.24 g, 0.74 mmol, 59%, oil). 1H NMR (300 MHz, CDCl3): delta 1.54 (m, 1H), 1.70-2.18 (m, 11H), 2.51 (m, 3H), 2.76 (m, 3H), 3.12 (m, 2H), 6.88 (d. J= 5.2 Hz, 1H), 7.04 (d, J= 5.2 Hz, 1H), 7.18-7.32 (m, 5H).
  • 33
  • [ 437998-28-2 ]
  • [ 10272-49-8 ]
  • [ 75-05-8 ]
  • [ 437995-23-8 ]
YieldReaction ConditionsOperation in experiment
With sodium cyanoborohydride; acetic acid; EXAMPLE 2 4-Phenylpiperidine hydrochloride (334 mg, 1.69 mmol) was added to the 10% aqueous acetonitrile solution of 8-chloro-1-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazoline-9(1H)-one (200 mg, 0.85 mmol), then sodium cyanoborohydride (133 mg, 2.11 mmol) and acetic acid (0.1 mL, 1.69 mmol) were added to the reaction mixture. The mixture was stirred at room temperature over night. The reaction mixture was extracted with ethyl acetate and washed with saturated sodium hydrogen carbonate aqueous solution and brine. The organic layer was dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by silica gel chromatography eluding with chloroform and methanol (100:5) to give 5-chloro-2-[3-(4-phenyl-1-piperidyl)propyl]-4(3H)-quinazolinone (96.6 mg, 0.25 mmol, 30%) as colorless solid. 1H NMR (300 MHz, CDCl3, delta): 1.88 (2H, m), 2.00 (2H, m), 2.25 (2H, m), 2.28 (5H, m), 2.60 (2H, m), 2.86 (2H, m), 3.19 (2H, m), 7.33-7.41 (6H, m), and 7.53 (2H, m). Mass (m/z): 382 (M++1)
  • 34
  • [ 697306-96-0 ]
  • [ 10272-49-8 ]
  • [ 530-62-1 ]
  • [ 697304-21-5 ]
  • C29H34N4O5 [ No CAS ]
  • C38H44N4O4 [ No CAS ]
  • 35
  • C18H20N4O3 [ No CAS ]
  • [ 10272-49-8 ]
  • [ 697304-21-5 ]
  • C29H34N4O5 [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 10272-49-8 ]

Aryls

Chemical Structure| 83949-37-5

A390846 [83949-37-5]

4-Methyl-4-phenylpiperidine hydrochloride

Similarity: 0.97

Chemical Structure| 771-99-3

A129207 [771-99-3]

4-Phenylpiperidine

Similarity: 0.97

Chemical Structure| 3973-62-4

A231594 [3973-62-4]

3-Phenylpiperidine

Similarity: 0.91

Chemical Structure| 430461-56-6

A323022 [430461-56-6]

(R)-3-Phenylpiperidine

Similarity: 0.91

Chemical Structure| 851000-46-9

A280161 [851000-46-9]

(R)-3-Phenylpyrrolidine hydrochloride

Similarity: 0.88

Related Parent Nucleus of
[ 10272-49-8 ]

Piperidines

Chemical Structure| 83949-37-5

A390846 [83949-37-5]

4-Methyl-4-phenylpiperidine hydrochloride

Similarity: 0.97

Chemical Structure| 771-99-3

A129207 [771-99-3]

4-Phenylpiperidine

Similarity: 0.97

Chemical Structure| 137730-67-7

A101379 [137730-67-7]

Spiro[indene-1,4'-piperidine] hydrochloride

Similarity: 0.91

Chemical Structure| 3973-62-4

A231594 [3973-62-4]

3-Phenylpiperidine

Similarity: 0.91

Chemical Structure| 430461-56-6

A323022 [430461-56-6]

(R)-3-Phenylpiperidine

Similarity: 0.91