Dichloromethane → (R)-1-[2-[3-(3,4-dichloro-phenyl)-1-(benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide

HRID 400072Notes

Reaction equation

HRID 400072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH2:22][CH2:23]CS([O-])(=O)=O)[CH2:13][CH2:12][N:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]([NH2:39])=[O:38])[CH2:33][CH2:32]1.[C:40]1([C:46]2([C:52]([OH:54])=[O:53])[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(OCC)(=O)C.ClCCl>CO.ClCCl>[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]([NH2:39])=[O:38])[CH2:33][CH2:32]1.[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH2:22][CH2:23][N:49]3[CH2:48][CH2:47][C:46]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)([C:52]([OH:54])=[O:53])[CH2:51][CH2:50]3)[CH2:13][CH2:12][N:11]([C:14](=[O:21])[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 675621544-Phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide hydrochlorideHCID 86753254(S)-2-[3-(3,4-dichloro-phenyl)-1-(benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate

Product 1

HCID 131720897(R)-1-[2-[3-(3,4-dichloro-phenyl)-1-(benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent4×

Procedure

Prepare by the method of Example 88.6 using (S)-2-[3-(3,4-dichloro-phenyl)-1-(benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate and 4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide hydrochloride to give, after chromatography on silica gel eluting sequentially with ethyl acetate, dichloromethane, 2% methanol/dichloromethane, 4% methanol/dichloromethane, 6% methanol/dichloromethane, and then 8% methanol/dichloromethane, the title compound: Rf =0.27 (silica gel, methanol/dichloromethane 1/9).

Workup

  1. customto give

Sources & evidence

ORD record
ord-af0e5feeed9341999439c72e771153fd
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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