193217-39-9|tert-Butyl 4-benzoylpiperidine-1-carboxylate| Ambeed

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Quality Control of [ 193217-39-9 ] Purity: 96% SDS Specification

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Product Details of [ 193217-39-9 ]

CAS No. :	193217-39-9
Formula :	C₁₇H₂₃NO₃
M.W :	289.37
SMILES Code :	CC(C)(C)OC(=O)N1CCC(CC1)C(=O)C1=CC=CC=C1
MDL No. :	MFCD09832216
InChI Key :	ITLCXSHKUNNAHG-UHFFFAOYSA-N
Pubchem ID :	10827307

Safety of [ 193217-39-9 ]

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

Application In Synthesis of [ 193217-39-9 ]

* 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 [ 193217-39-9 ]

[ 193217-39-9 ] Synthesis Path-Downstream 1~35

1
[ 24424-99-5 ]
[ 25519-80-6 ]
[ 193217-39-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium hydrogencarbonate; In H2 O-TBF;	I. Preparation of 4-benzoyl-N-t-butoxylcarbonylpiperidine (compound 86) A mixture of 4-benzoylpiperidine hydrochloride (6.77 g, 30.0 mmol), di-tert-butyldicarbonate (7.2 g, 33.0 mmol) and KHCO3 (6.0 g, 60 mmol) in H2 O--TBF (50/20 mL) was refluxed for 1 h. The reaction mixture was extracted with ethyl acetate (2*100 mL). The combined organic layers were washed with brine, dried over MgSO4. Removal of solvents gave 4-benzoyl-N-t-butoxylcarbonyl-piperidine (8.54 g, 98%); δH (400 MHz, CDCl3) 1.47 (s, 9H), 1.70 (m, 2H), 1.83 (m, 2H), 2.91 (m, 2H), 3.42 (m, 2H), 4.18 (brs, 2H), 7.46 (m, 2H), 7.56 (m, 1H), 7.93 (m, 2H).
94%	With triethylamine; In acetonitrile; at 25℃; for 16h;	Synthesis of tert-butyl 4-benzoylpiperidi -carboxylate4-Benzoylpiperidine · HC1 (400 mg, 1.78 mmol) was dissolved in acetonitrile (8 mL).Triethylamine (1.25 mL, 8.9 mmol) and di-tert-butyl dicarbonate (465 mg, 2.13 mmol) was added and the reaction was stirred at 25 C for 16 hours. Concentrated reaction mixture under reduced pressure and partitioned between EtOAc (40 mL) and 0.5 M HC1 (20 mL). Discarded aqueous layer and then washed with saturated aqueous sodium bicarbonate (20 mL) followed by brine (20 mL). Dried with MgSC and then under reduced pressure to give the title compound; white solid (484 mg, 94%) NMR (400 MHz, CHLOROFORM-d) δ ppm 7.94 (d, 7=7.53 Hz, 2 H), 7.58 (t, 7=7.00 Hz, 1 H), 7.48 (t, 7=7.50 Hz, 2 H), 4.17 (br. s, 2 H), 3.35 - 3.47 (m, 1 H), 2.79 - 2.99 (m, 2 H), 1.78 - 1.91 (m, 2 H), 1.65 - 1.78 (m, 2 H), 1.47 (s, 9 H)
66%	With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 3h;	To a mixture of 4-benzoylpiperidine hydrochloride (8, 4.0 g, 17.72 mmol) in THF (48 mL) were added di-tert-butyl dicarbonate (5.2 g, 24.81 mmol), triethylamine (7.4 mL, 53.16 mmol), and 4-dimethylaminopyridine (649 mg, 5.32 mmol) and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, THF was concentrated and EtOAc and water were added. It was extracted with EtOAc and the organic phase was collected, dried over MgSO4, filtered and concentrated. Silica gel column chromatography (EA:HX = 1:5) was done to get 9-2 (3.29 g, 66%- 3 -yield) as a white solid. 1H NMR (CDCl3) δ 7.97-7.90 (m, 2H), 7.51 (ddd, J = 14.8, 7.7, 6.4 Hz, 3H), 4.16 (d, J = 13.3 Hz, 2H), 3.40 (ddd, J = 11.0, 7.4, 3.9 Hz, 1H), 2.98-2.82 (m, 2H), 1.91-1.59 (m, 4H), 1.47 (s, 9H).

5 g

With triethylamine; In dichloromethane; at 20℃; for 4h;

Step 1:5 To a stirred solution of 4-benzoylpiperidinium chloride (5 g) in dry DCM (50 mL),triethylamine (11 mL) and Boc anhydride (6.7 g) were added. The reaction mixture wasstirred at room temperature for 4 hours and diluted with water (50 mL ). The aqueousphase was extracted with dichloromethane (2 x 25 mL ). The combined organic layer waswashed with brine ( 5 OmL) and dried over anhydrous N a2S04. Evaporation of solvents10 under reduced pressure gave crude product, which was treated with hexane to obtainsolid. The solid obtained was filtered, washed with cold hexane (50 mL) and dried undervacuum to get tert-butyl4-benzoylpiperidine-1-carboxylate (5 g) as white solid. 1H NMR(CDCh): o 1.51 (s, 9H), 1.67-1.76 (m, 2H), 1.85-1.88 (m, 2H), 2.87-2.94 (m, 2H), 3.39-3.45 (m, 1H), 4.16-4.19 (m, 1H), 7.47-7.60 (m, 3H), 7.94-7.96 (m, 2H).

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3878 - 3894.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 3895 - 3905.
[3]Patent: US6130222,2000,A .
[4]Patent: WO2011/123937,2011,A1 .Location in patent: Page/Page column 105.
[5]Journal of Organic Chemistry,2006,vol. 71,p. 7035 - 7044.
[6]Bioorganic Chemistry,2021,vol. 110.
[7]Journal of Medicinal Chemistry,2008,vol. 51,p. 2147 - 2157.
[8]Patent: WO2014/25854,2014,A1 .Location in patent: Page/Page column 63; 64.

2
[ 77350-52-8 ]
[ 193217-39-9 ]
[ 193217-40-2 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3878 - 3894.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 3895 - 3905.

3
[ 37586-22-4 ]
[ 24424-99-5 ]
[ 193217-39-9 ]

Yield	Reaction Conditions	Operation in experiment
90%		To a mixture of NaHC03 (173 g) and water (1.5 L) was added compound 11a of J. Med. Chem. 2003, vol 46, 25, 5512-5532 (119.3 g, 0.63 mol). The reaction was stirred at room temperature for 15 min and then (Boc)20 was added. After stirring for 15 h at room temperature a white solid was filtered and washed with water to affor 164 g (Yield: 90 %, mp 91-93 C) of 4-benzoyl-l-[(l,l-dimethylethyloxy)carbonyl]piperidine. A suspension of Mg turnings (1.0 g) in anhydrous diethyl ether (40 mL) was prepared and treated with 1/3 of a solution of 4-chlorobenzyl chloride (4.6 g, 27.0 mmol) in anhydrous diethyl ether (40 mL) and an iodine crystal. The mixture was heated until a smooth reflux was observed and the color disappeared. The rest of the solution of 4- chlorobenzyl chloride was added. The reflux was continued for 3.5 h and the reaction mixture cooled to room temperature. A solution of 4-benzoyl-l-[(l,l- dimethylethyloxy)carbonyl]piperidine (6.4 g, 22.4 mmol) in anhydrous diethyl ether (50 mL) was added dropwise and the reaction refluxed for 3h. A saturated aqueous NH4C1 solution (50 mL) was added, the diethyl ether evaporated and the mixture extracted with CHC13. The organic layer was dried over anhydrous Na2S04, filtered and concentrated in vacuo to give to give a solid which was washed with hexane. This solid was dissolved in chloroform (100 mL), treated with trifluoro acetic acid (8 mL) and refluxed for 15 h. The reaction mixture was cooled to room temperature, treated with 10 % aqueous NaOH solution and extracted with chloroform. The organic layer was dried over anhydrous Na2S04, filtered and evaporated under reduced pressure to afford a mixture E/Z isomers. Purification by flash chromatography on silica gel (Diethyl etherTsopropilamine 10/0.5) gave 1.6 g of the Z isomer of the title compound (Yield: 22 %, mp 121-124 C).
	With sodium hydroxide; In water; at 20℃; for 18h;	Method I Preparation of 3-phenyl-3-(1-tert-butylcarbonyloxypiperidin-4-yl)propionaldehyde; Step 1: Preparation of 1-tert-butylcarbonyloxy-4-benzoylpiperidine To a solution of 4-benzoylpiperidine (6 g, 26.5 mmol) in 2M aqueous sodium hydroxide (26.5 mL) was added di-tert-butyl dicarbonate (5.79 g, 26.5 mmol) and the resulting mixture was stirred at room temperature for 18 h. The solid product was isolated by filtration and dried under vacuum at 40 C. giving the sub-titled compound (7 g); NMR: 1.3-1.4 (m, 11H) 1.7 (m, 2H) 2.9 (m, 2H) 3.6 (m, 1H) 3.95 (m, 2H) 7.5-7.6 (m, 3H) 7.95 (d, 2H). Step 2: Preparation of ethyl 3-phenyl-3-(1-tert-butylcarbonyloxypiperidin-4-yl)acrylate

References: [1]Patent: WO2011/147780,2011,A1 .Location in patent: Page/Page column 30.
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 5512 - 5532.
[3]Patent: US2007/167442,2007,A1 .Location in patent: Page/Page column 36.

4
[ 193217-39-9 ]
[ 269741-35-7 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 5512 - 5532.
[2]Journal of Organic Chemistry,2006,vol. 71,p. 7035 - 7044.
[3]RSC Advances,2014,vol. 4,p. 17293 - 17299.

5
[ 193217-39-9 ]
tert-butyl (S)-4-(hydroxy(phenyl)methyl)piperidine-1-carboxylate [ No CAS ]
tert-butyl (R)-4-(hydroxy(phenyl)methyl)piperidine-1-carboxylate [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7035 - 7044.

6
[ 193217-39-9 ]
[ 957202-21-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 4 Synthesis of (S)-phenyl(piperidin-4-yl)methanol (1S)-(+)10-camphorsulfonic acid salt; To a solution of (-)-DIPCl (315 mL, 0.57 mol, 63.6 % in heptane) in THF anhydrous (1 1), 4-(benzoyl)piperidine-1-carboxylic acid tert-butyl ester (75.0 g, 0.26 mol) was added at room temperature. After 21 hours acetaldehyde (55 mL) was added, stirring continued for 3 h at room temperature and then 25 % aq NaOH added and the mixture stirred for 45 min. The organic phase was separated, washed with brine, the solvent removed under reduced pressure and the residue treated with dichloromethane. The aqueous phase was treated with 30 % aqueous NaOH, extracted with dichloromethane, dried, filtered and concentrated to give a brown oil (56 g) wich was dissolved in THF (300 mL), treated with (1S)-(+)-camphorsulphonic acid (51.9 g) and heated until 85 C. After 20 h at room temperature a white solid was filtered (mp 148.1-150.9 C, yield: 55.3 %, 99.9 % ee)

References: [1]Patent: EP1854785,2007,A1 .Location in patent: Page/Page column 7.

7
[ 681135-25-1 ]
[ 100-59-4 ]
[ 193217-39-9 ]

Yield	Reaction Conditions	Operation in experiment
21%	In tetrahydrofuran; at -40 - 25℃;	To a stirring solution of tert-butyl 4-(methoxy (methyl) carbamoyl) piperidine-1-carboxylate (0.133 g, 0.488 mmol) in THF (1 mL) at -400C was added phenylmagnesium chloride (0.269 mL, 0.537 mmol, 2M in THF) dropwise. The mixture was allowed to warm up to room temperature and was quenched with aqueous saturated ammonium chloride, then extracted with AcOEt (2X) . The crude product was purified by chromatography on silica gel (20% AcOEt/hexanes) to give tert- <n="148"/>butyl 4-benzoylpiperidine-l-carboxylate (0.030 g, 21%) as an oil: 1H NMR (400 MHz, CDCl3) δ 1-47 (s, 9H), 1.72 (m, 2H), 1.84 (m, 2H), 2.90 (m, 2H), 3.41 (m, IH), 4.16 (br, 2H), 7.48 (m, 2H), 7.58 (m, IH), 7.94 (m, 2H).

References: [1]Patent: WO2008/11130,2008,A2 .Location in patent: Page/Page column 146-147.

8
[ 193217-39-9 ]
[ 25519-80-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride; In 1,4-dioxane; at 18 - 25℃; for 0.5h;	To this oil was added HCl (2.59 mL, 10.4 ϖαnol, 4M in dioxane) and the solution was stirred for 30 minutes at room temperature. The solvent was removed in vacuo to give phenyl (piperidin-4-yl)methanone hydrochloride (0.023 g, 98%) as a solid: 1H NMR (400 MHz, DMSO- d6) δ 1.75 (m, 2H), 1.95 (m, 2H), 3.04 (m, 2H), 3.48 (m, 2H), 3.69 (m, 2H), 3.77 (m, IH), 7.56 (m, 2H), 7.68 (m, IH), 8.00 (m, 2H) .

References: [1]Patent: WO2008/11130,2008,A2 .Location in patent: Page/Page column 147.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 341 - 345.

9
[ 59084-16-1 ]
[ 193217-39-9 ]