Citric Acid → 3-(1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate
Reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:14]2)=[O:12])[CH2:5][CH2:4]1.[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38]>C(O)C>[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38].[CH3:1][N:2]([CH3:34])[C:3]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:14]2)=[O:12])[CH2:5][CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The polar diastereoisomer of 3-(1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (214 mg, 0.467 mmole) was dissolved in abs. ethanol (3 ml). Citric acid (90.6 mg, 0.471 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. Ethanol was distilled off down to a volume of 1 ml. Diethyl ether (10 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 3-(1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate (297 mg, m.p. 116°-120° C., 98%, Example 48) was a cream-coloured solid.