1-Propanesulfonate → 1-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide hydrochloride

HRID 400033

Reaction equation

HRID 400033 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:28][CH2:29]CS([O-])(=O)=O)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(CS([O-])(=O)=O)C.Cl.[CH3:43][N:44]1[CH2:49][CH2:48][N:47]([C:50]([NH2:52])=[O:51])[CH2:46][CH2:45]1.[C:53]1([C:59]2([C:65]([OH:67])=[O:66])[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.C(OCC)(=O)C.CCCCCC>CO.ClCCl>[ClH:1].[CH3:43][N:44]1[CH2:49][CH2:48][N:47]([C:50]([NH2:52])=[O:51])[CH2:46][CH2:45]1.[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:28][CH2:29][N:62]3[CH2:61][CH2:60][C:59]([C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=4)([C:65]([OH:67])=[O:66])[CH2:64][CH2:63]3)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 44317561-PropanesulfonateHCID 21226206Ethyl acetate hexaneHCID 675621544-Phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide hydrochlorideHCID 867509062-[1-(3,4,5-Trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate

Product 1

HCID 675622111-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent2×

Procedure

Prepare by the method of example 27.3.1 using 2-[3-(3,4-dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate (2.8 g, 5.24 mmol) and 4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide pyrrolidin-3-yl]-ethyl-methanesulfonate (2.8 g, 5.24 mmol) and 4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide hydrochloride (2.8 g, 3.9 mmol). Chromatograph on silica gel eluting sequentially with 50% ethyl acetate/hexane, 3% methanol/dichloromethane, and then 6% methanol/dichloromethane to give the title compound.

Sources & evidence

ORD record
ord-c8a52108f6f846b09832c344e0562d86
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Linked notes

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