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

HRID 2357484Notes

Reaction equation

HRID 2357484 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]1

Participants

4

Reactant 2

HCID 311Citric AcidHCID 593855643-(1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide

Product 1

HCID 675314873-(1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. stirringThe reaction mixture was stirred for 2 hours at RT
  2. customDuring this time no precipitate formed
  3. distillationEthanol was distilled off down to a volume of 1 ml
  4. additionDiethyl ether (10 ml) was added to the residue
  5. stirringThe suspension was stirred for 20 hours at RT
  6. filtrationThe precipitate was filtered off
  7. washwashed with diethyl ether (3×1.5 ml)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-0c7295416d1d4914adbf017da2c613c0
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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