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

HRID 399982Notes

Reaction equation

HRID 399982 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:29][CH2:30]CS([O-])(=O)=O)[CH2:14][CH2:13][N:12]([C:15](=[O:28])[C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=4)[CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[C:37]1([C:43]2([C:49]([NH2:51])=[O:50])[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(OCC)(=O)C.CCCCCC>CO.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:29][CH2:30][N:46]4[CH2:45][CH2:44][C:43]([C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)([C:49]([NH2:51])=[O:50])[CH2:48][CH2:47]4)[CH2:14][CH2:13][N:12]([C:15](=[O:28])[C:16]4[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=4)[CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 30171294-Phenylpiperidine-4-carboxamide monohydrochlorideHCID 21226206Ethyl acetate hexaneHCID 867509132-[3-(Benzo[1,3]dioxol-5-yl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate

Product 1

HCID 544401831-[2-[3-(Benzo[1,3]dioxol-5-yl)-1-(3,4,5-trimethoxy-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-(benzo[1,3]dioxol-5-yl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate (0.22 g, 0.43 mmol) and 4-phenyl-piperidine-4-carboxylic acid amide hydrochloride (0.21 g, 0.86 mmol). Chromatograph on silica gel eluting sequentially with 50% ethyl acetate/hexane and then 6% methanol/dichloromethane to give the title compound: Rf =0.38 (silica gel, 10% methanol/dichloromethane).

Sources & evidence

ORD record
ord-2520b66fa18a4bea8d396d8d7b0ca147
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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