4-Phenylpiperidine-4-carboxamide monohydrochloride → 1-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trifluoro-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid amide

HRID 2258776Notes

Reaction equation

HRID 2258776 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:25][CH2:26]CS([O-])(=O)=O)[CH2:13][CH2:12][N:11]([C:14](=[O:24])[C:15]3[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[C:33]1([C:39]2([C:45]([NH2:47])=[O:46])[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(OCC)(=O)C.CCCCCC>CO.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:25][CH2:26][N:42]3[CH2:41][CH2:40][C:39]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)([C:45]([NH2:47])=[O:46])[CH2:44][CH2:43]3)[CH2:13][CH2:12][N:11]([C:14](=[O:24])[C:15]3[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 30171294-Phenylpiperidine-4-carboxamide monohydrochlorideHCID 21226206Ethyl acetate hexaneHCID 867509312-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trifluoro-benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate

Product 1

HCID 544965181-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trifluoro-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepare by the method of example 27.3.1 using 2-[3-(3,4-dichloro-phenyl)-1-(3,4,5-trifluoro-benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate (1 mmol) and 4-phenyl-piperidine-4-carboxylic acid amide hydrochloride (0.29 g, 1.2 mmol). Chromatograph on silica gel eluting sequentially with 50% ethyl acetate/hexane and then 6% methanol/dichloromethane to give the title compound:

Sources & evidence

ORD record
ord-fd923819c2df42a6abbb618b0a256d71
Source dataset
uspto-grants-1997_08
Patent number
US05661160

Reaction notes

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