446302-83-6|1-Benzyl-3-phenylpiperidin-4-one| Ambeed

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Quality Control of [ 446302-83-6 ] Purity: 97% SDS Specification

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Product Details of [ 446302-83-6 ]

CAS No. :	446302-83-6
Formula :	C₁₈H₁₉NO
M.W :	265.35
SMILES Code :	O=C1C(C2=CC=CC=C2)CN(CC3=CC=CC=C3)CC1
MDL No. :	MFCD11111091
InChI Key :	VDRJIVUPMPNZBO-UHFFFAOYSA-N
Pubchem ID :	11817956

Safety of [ 446302-83-6 ]

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

Computational Chemistry of [ 446302-83-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	12
Fraction Csp3	0.28
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	84.83
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.31 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.7
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	2.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.71
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.	2.93
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	3.74
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.0

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.56
Solubility	0.0723 mg/ml ; 0.000273 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.	-3.0
Solubility	0.267 mg/ml ; 0.00101 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	-5.7
Solubility	0.000526 mg/ml ; 0.00000198 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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.	-5.85 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<0.0
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)	2.24

Application In Synthesis of [ 446302-83-6 ]

* 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 [ 446302-83-6 ]

[ 446302-83-6 ] Synthesis Path-Downstream 1~35

1
[ 446302-83-6 ]
[ 76041-09-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; at 40℃; under 3750.38 Torr; for 3.0h;	A solution of the compound (2.00 g) obtained in Process 3, hydrochloric acid (0.2 ml) and palladium carbon (10 wtpercent, 0.30 g) in ethanol (30 ml) was stirred at 40°C for 3 hours under hydrogen atmosphere of 0.5 MPa. The catalyst was removed by filtration, and then the reaction solution was concentrated under reduced pressure to obtain crude 3-phenyl-4-piperidone as pale yellow powder. The obtained product was used in the next process without further purification.

References: [1]European Journal of Organic Chemistry,2007,p. 4376 - 4382.
[2]Patent: EP1553084,2005,A1 .Location in patent: Page/Page column 44.

2
[ 907997-09-5 ]
[ 100-46-9 ]
[ 446302-83-6 ]

References: [1]European Journal of Organic Chemistry,2007,p. 4376 - 4382.
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 420 - 431.

3
[ 446302-83-6 ]
tert-butyl (3R)-3-piperazin-1-ylpyrrolidine-1-carboxylate [ No CAS ]
C₃₁H₄₄N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of intermediate compound 27 (0.02 mol) in a small amount OF CH2CK WAS added to 3-PHENYL-1-(PHENYLMETHYL)-4-PIPERIDINONE (0.02 mol) and the mixture was stirred, toluene was added and the reaction mixture was evaporated. Titanium, tetrakis (2-PROPANOLATO) (0.025 mol) was added to the residual oil and the mixture was stirred for 3 hours at 50C, EtOH, p. a. (30 ml) was added and the resulting mixture was stirred for 15 min. at room temperature. Finally NaBH3CN (0.04 mol) was added and the reaction mixture was stirred for 20 hours at room temperature. The mixture was washed with a basic NAOH solution and CH2CI2 was added. The resulting mixture was stirred for 15 min. and after addition of dicalite the mixture was filtered over dicalite. The organic layer was separated, dried (MGS04), filtered off and the solvent was evaporated. The residue was purified over silica gel on a glass filter (gradient eluent: CH2C12/CH3OH 100/0-> 90/10). The product fractions were collected and the solvent was evaporated. Yield: 6.4 g of intermediate 28.

References: [1]Patent: WO2004/56799,2004,A2 .Location in patent: Page 39-40.

4
[ 632352-55-7 ]
[ 446302-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; acetic acid; at 120℃; for 12.0h;	To a solution of the compound (15.0 g) obtained in Process 2 in acetic acid (90 ml), concentrated hydrochloric acid (90 ml) was added, and the reaction mixture was stirred at 120°C for 12 hours. The reaction mixture was concentrated under reduced pressure, and then into the obtained residue was poured ethyl acetate, and made basic with an aqueous sodium hydroxide solution. The organic layer was washed with saturated brine, dried, and then the solvent was evaporated under reduced pressure to obtain 1-benzyl-3-phenyl-4-piperidinone as colorless oil (10.4 g). 1H-NMR (CDCl3): delta 2.47 - 2.85 (4H, m), 3.00-3.25 (2H, m), 3.67 (2H, s), 3, 81 (1H, dd, J=10.0, 5.6 Hz), 7.19-7.40 (10H, m).

References: [1]Patent: EP1553084,2005,A1 .Location in patent: Page/Page column 43.

5
[ 110-85-0 ]
[ 446302-83-6 ]
tetra-isopropyl-orthotitanate [ No CAS ]
rac-cis-1-(1-benzyl-3-phenyl-piperidin-4-yl)-piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With triethylamine; In dichloromethane; water; ethylene glycol;	EXAMPLE 32 Rac-cis-1-{4-[1-(3,5-Bis-trifluoromethyl-benzoyl)-3-phenyl-piperidin-4-yl]-piperazin-1-yl}-2,2,2-trifluoro-ethanone To a mixture of <strong>[446302-83-6]1-benzyl-3-phenyl-piperidin-4-one</strong> (10.0 g, 37.7 mmol) and piperazine (13.0 g, 151 mmol) was added tetraisopropyl-orthotitanate (42.8 mL, 151 mmol) at room temperature. After stirring at room temperature overnight the reaction mixture was diluted with ethanol (300 mL) and sodium cyanoborohydride (10.5 g, 151 mmol) was added. The reaction mixture was stirred at room temperature for 24 h and was diluted with water (10 mL). The inorganic precipitate was filtered off and washed with ethanol. The solvent was evaporated and the residue was taken up in ethylenglycol (130 mL) and sodium hydroxide (13.6 g, 37.7 mmol) was added. The reaction mixture was stirred at 130° C. for 15 min. After cooling water (200 mL) was added and the mixture was extracted twice with 200 mL diethylether. Organic phases were pooled, dried with magnesium sulfate and evaporated. Flash chromatography on silica gel with methylene chloride/triethyl amine 99:1 gave rac-cis-1-(1-benzyl-3-phenyl-piperidin-4-yl)-piperazine (4.63 g, 36percent), as a yellow oil, MS: m/e=336.3 (M+H+).

References: [1]Patent: US2002/151547,2002,A1 .

6
[ 446302-83-6 ]
[ 1215036-17-1 ]

References: [1]Tetrahedron Asymmetry,2009,vol. 20,p. 2724 - 2727.
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 420 - 431.

7
[ 446302-83-6 ]
[ 632352-56-8 ]