Citric Acid → 4-(5-methoxy-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate

반응식

[CH3:1][N:2]([CH3:36])[C:3]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:5][CH2:4]1.C(O)C.[C:40]([OH:52])(=[O:51])[CH2:41][C:42]([CH2:47][C:48]([OH:50])=[O:49])([C:44]([OH:46])=[O:45])[OH:43]>C(Cl)Cl>[C:40]([OH:52])(=[O:51])[CH2:41][C:42]([CH2:47][C:48]([OH:50])=[O:49])([C:44]([OH:46])=[O:45])[OH:43].[CH3:36][N:2]([CH3:1])[C:3]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:14][CH2:15][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:5][CH2:4]1

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실험 절차

The polar diastereoisomer of 4-(5-methoxy-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (197 mg, 0.403 mmole) was dissolved in abs. ethanol (3 ml) and DCM (5 ml). Citric acid (78.3 mg, 0.407 mmole) was added in one portion at ca. 40° C. while stirring. The reaction mixture was stirred for 2 hours at RT. During this time no precipitate formed. The solvents were distilled off down to a volume of 2 ml. Diethyl ether (30 ml) was added to the residue. The suspension was stirred for 20 hours at RT. The precipitate was filtered off, washed with diethyl ether (3×1.5 ml) and dried in vacuo. The polar diastereoisomer of 4-(5-methoxy-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate (239 mg, m.p. 139°-143° C., 87%, Example 46) was a colourless solid.