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

HRID 343707Notes

Reaction equation

HRID 343707 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:31][CH2:32]CS([O-])(=O)=O)[CH2:13][CH2:12][N:11]([C:14](=[O:30])[C:15]3[CH:20]=[C:19]([O:21][CH2:22][CH3:23])[C:18]([O:24][CH2:25][CH3:26])=[C:17]([O:27][CH2:28][CH3:29])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[C:39]1([C:45]2([C:51]([NH2:53])=[O:52])[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(OCC)(=O)C.CCCCCC>CO.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:31][CH2:32][N:48]3[CH2:47][CH2:46][C:45]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)([C:51]([NH2:53])=[O:52])[CH2:50][CH2:49]3)[CH2:13][CH2:12][N:11]([C:14](=[O:30])[C:15]3[CH:20]=[C:19]([O:21][CH2:22][CH3:23])[C:18]([O:24][CH2:25][CH3:26])=[C:17]([O:27][CH2:28][CH3:29])[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 867509292-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-triethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate

Product 1

HCID 544187311-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-triethoxy-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-triethoxy-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: Rf =0.36 (silica gel, 10% methanol in dichloromethane). Exact mass (FAB+): calculated for C37H46Cl2N3O5 calculated 682.2815. Found 682.2799.

Sources & evidence

ORD record
ord-8d05642cadf547668ab4a9cdceeaf2fe
Source dataset
uspto-grants-1999_01
Patent number
US05861416

Reaction notes

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