72551-53-2|Ethyl 1-benzylpiperidine-3-carboxylate| Ambeed

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Quality Control of [ 72551-53-2 ] Purity: 98% SDS Specification

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Product Details of [ 72551-53-2 ]

CAS No. :	72551-53-2
Formula :	C₁₅H₂₁NO₂
M.W :	247.33
SMILES Code :	O=C(C1CN(CC2=CC=CC=C2)CCC1)OCC
MDL No. :	MFCD00191221
InChI Key :	CDMAVYOAEITWFQ-UHFFFAOYSA-N
Pubchem ID :	2736370

Safety of [ 72551-53-2 ]

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

Computational Chemistry of [ 72551-53-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	6
Fraction Csp3	0.53
Num. rotatable bonds	5
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	75.85
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.54 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.15
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.93
Log P_o/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.	2.38
Log P_o/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	2.73
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.53

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.85
Solubility	0.352 mg/ml ; 0.00142 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.	-2.73
Solubility	0.456 mg/ml ; 0.00184 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	-3.78
Solubility	0.0408 mg/ml ; 0.000165 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	No
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.	-6.06 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	0.0
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)	2.35

Application In Synthesis of [ 72551-53-2 ]

* 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 [ 72551-53-2 ]

[ 72551-53-2 ] Synthesis Path-Downstream 1~35

1
[ 71962-74-8 ]
[ 72551-53-2 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 515 - 516.

2
[ 151-50-8 ]
[ 72551-53-2 ]
[ 132462-28-3 ]
[ 132462-28-3 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 2386 - 2390.

3
[ 151-50-8 ]
[ 72551-53-2 ]
[ 132462-28-3 ]

References: [1]Tetrahedron,1992,vol. 48,p. 9753 - 9766.

4
[ 72551-53-2 ]
[ 460-00-4 ]
[ 117022-68-1 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 105 - 118.

6
[ 67-56-1 ]
[ 72551-53-2 ]
[ 94379-05-2 ]
[ 50585-89-2 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5645 - 5649.

7
[ 72551-53-2 ]
[ 94379-05-2 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5645 - 5649.

8
[ 72551-53-2 ]
[ 182919-58-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrazine hydrate; In ethanol;Reflux;	A mixture of <strong>[72551-53-2]ethyl 1-benzylpiperidine-3-carboxylate</strong> (9) (5.1 g,20.62 mmol, 1 eq.) and hydrazine monohydrate (10 mL, 10 eq.) inethanol (10 mL) was stirred overnight under reflux. After cooling,the solvent and excess of hydrazine were removed under reducedpressure to afford compound 10 as colorless oil in yield of 99%; 1HNMR (400 MHz, CDCl3) delta 9.00 (s br, 1H, NH), 7.32e7.17 (m, 5H, Ar-H), 3.79 (s br, 2H, NH2), 3.47 (d, J 12.4 Hz, 1H, CHa-Ph), 3.38 (d,J 12.4 Hz, 1H, CHb-Ph), 2.62 (m, 2H, piperidin-H), 2.45 (m, 1H,piperidin-H), 2.23 (m, 2H, piperidin-H), 1.87 (m, 1H, piperidin-H),1.72-1.48 (m, 3H, piperidin-H); 13C NMR (100 MHz, CDCl3)delta 175.4, 137.3, 129.2, 128.4, 127.4, 63.4, 54.4, 53.7, 40.8, 26.7, 22.7;HRESI-MS m/z calcd. for [M+H]+ C13H20N3O: 234.1601, found:234.1604.
92%	With acetic acid; hydrazine; In ethanol; for 72h;Heating / reflux;	Acetic acid (20 mL) and hydrazine hydrate (136 mL (140 g, 2.8 mol) were added to a solution of (3RS)- ethyl l-(phenylmethyl)-3-piperidinecarboxylate (Description 72, 270 g, 1.092 mol) in ethanol (310 mL) and the mixture was heated under reflux for 3 days. The mixture was cooled and the solvent was partly evaporated under reduced pressure until a precipitation occurred. The solid was collected, aqueous KOH (50 g in 100 mL) was added and the mixture was extracted with CHCl3 (2 x 300 mL). The combined organic fractions were dried (Na2SO4) the solvent was partly evaporated under reduced pressure until a precipitation occurred. The solid was collected, the filtrate was diluted with Et2O (200 mL) and further solid was collected. The combined solids were washed with Et2O and dried in vacuo to give the title compound as a solid (217 g, 92%).
	With hydrazine hydrate; In ethanol;Reflux;	General procedure: Each ethyl N-substituted nipecotate derivative/ethyl N-substitutedisonipecotate derivative (1 mol) in 30 mL ethanol and hydraziniumhydroxide (10 mol) were heated under microwave irradiation (130 C,300 W) or refluxed for 24-48 h in an oil bath. After completion of thereaction (TLC), ethanol was evaporated and the residue was extractedwith dichloromethane or diethyl ether. The solvent was evaporatedunder reduced pressure until an oily residue occured. Then n-hexanewas added to the residue to give the title compound as a white solid.The precipitated crystals were separated by filtration.

References: [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 972 - 985.
[2]Tetrahedron Letters,2001,vol. 42,p. 5645 - 5649.
[3]Patent: WO2007/3965,2007,A1 .Location in patent: Page/Page column 35.
[4]Bioorganic Chemistry,2019,vol. 87,p. 888 - 900.

9
[ 100-39-0 ]
[ 71962-74-8 ]
[ 72551-53-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium carbonate; In dichloromethane; water; for 3h;Reflux;	To a solution of ethyl nipecotate (5.94 mL, 38.24 mmol,1 eq.) in amixture of DCM (80 mL) and H2O (40 mL), benzyl bromide(4.77 mL, 1.05 eq.) and Na2CO3 (5.06 g, 1.25 eq.) were added and theresulting reaction mixture was refluxed for 3 h. The organic layerwas separated from aqueous layer, washed with brine, dried overMgSO4, and evaporated under reduced pressure. The residue waspurified by flash chromatography on silica gel using a mixture ofethylactate, hexanes (1:6) as eluent to give 9 as colorless oil in yieldof 87%; 1H NMR (400 MHz, CDCl3) delta 7.29-7.18 (m, 5H, Ar-H), 4.11 (q,J 7.2 Hz, 2H, OCH2CH3), 3.51 (d, J 13.6 Hz, 1H, CHa-Ph), 3.44 (d,J 13.2 Hz, 1H, CHb-Ph), 2.90 (m, 1H, piperidin-H), 2.68 (m, 1H,piperidin-H), 2.54 (m, 1H, piperidin-H), 2.20 (m, 1H, piperidin-H),2.01 (m, 1H, piperidin-H), 1.90 (m, 1H, piperidin-H), 1.69 (m, 1H,piperidin-H), 1.52 (m, 2H, piperidin-H), 1.19 (t, J 7.2 Hz, 3H,OCH2CH3); 13C NMR (62.5 MHz, CDCl3): delta 174.4, 138.4, 129.1, 128.2,127.0, 63.3, 60.3, 55.5, 53.7, 42.0, 27.0, 24.6, 14.2; HRESI-MS m/zcalcd. for [M+H]+ C15H22NO2: 248.1645, found: 248.1646.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 20h;	EXAMPLE 34 Preparation of ethyl 1-Benzyl-3-piperidinecarboxylate Commercially available ethyl nipecotate (509.7 mg; 3.25 mmol) was dissolved in dichloromethane (12 ml).. Dilsopropylethylamine (570 mul; 3.27 mmol) was added, followed by commercially available benzyl bromide (386 mul; 3.25 mmol) and the mixture stirred at ambient temperature for approximately 20 hours.. The mixture was then evaporated at ambient temperature under reduced pressure.. The crude product was purified by chromatography on silica eluding with 80% ethyl acetate in hexane, giving ethyl 1-benzyl-3-piperidinecarboxylate (634.4 mg) as a colorless oil. MS m/z (positive ion) 248 (MH+; 100).

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 5512 - 5532.
[2]Journal of Organic Chemistry,2016,vol. 81,p. 11235 - 11249.
[3]Tetrahedron Letters,2001,vol. 42,p. 5645 - 5649.
[4]European Journal of Medicinal Chemistry,2017,vol. 127,p. 972 - 985.
[5]Patent: US6664271,2003,B1 .Location in patent: Page column 15.

10
[ 72551-53-2 ]
[ 141943-04-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; at 20℃;	A 4N-aqueous sodium hydroxide solution (15 ml) was added to a solution of <strong>[72551-53-2]ethyl 1-benzyl-3-piperidinecarboxylate</strong> (7.00 g, 28.3 mmol) in a mixture of tetrahydrofuran (30 ml) and 1,4-dioxane (30 ml), and the resulting mixture was stirred at room temperature for 4 hours. After a 4N-aqueous sodium hydroxide solution (15 ml) was added again, the resulting mixture was stirred overnight at room temperature. After completion of the reaction, the reaction solution was neutralized by the addition of 2N-hydrochloric acid (15 ml) under ice-cooling and the resulting mixture was subjected to azeotropic concentration with toluene. The residue was suspended in ethanol, followed by filtration, and the filtrate was concentrated to obtain 1-benzyl-3-piperidinecarboxylic acid (6.3 g, 100%).
	With hydrogenchloride; water; for 4h;Heating / reflux;	Step 1: l-Benzylpiperidine-3-carbonyl chloride hydrochloride; [00273] Hydrochloric acid (20 % aq, 100 mL) was added to ethyl l-benzylpiperidine-3- carboxylate (14.2 g, 57.4 mmol) and the mixture heated at reflux for 4 h. The reaction was cooled and concentrated in vacuo to give l-benzylpiperidine-3-carboxylic acid as a pale yellow solid. This solid was dissolved in thionyl chloride and the resulting solution stirred at room temperature for 1 h. Thionyl chloride was removed in vacuo and the resulting solid was slurried in THF and azeotroped to afford the title compound as a pale yellow solid which was used without further purification (17.0 g, quant.).

References: [1]Patent: EP1403255,2004,A1 .Location in patent: Page 66.
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 5512 - 5532.
[3]Patent: WO2008/55959,2008,A1 .Location in patent: Page/Page column 65.

11
[ 72551-53-2 ]
[ 769907-38-2 ]