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

HRID 2357450Notes

Reaction equation

HRID 2357450 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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]([Cl:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:5][CH2:4]1.C(O)C.[C:39]([OH:51])(=[O:50])[CH2:40][C:41]([CH2:46][C:47]([OH:49])=[O:48])([C:43]([OH:45])=[O:44])[OH:42]>C(OCC)C>[C:39]([OH:51])(=[O:50])[CH2:40][C:41]([CH2:46][C:47]([OH:49])=[O:48])([C:43]([OH:45])=[O:44])[OH:42].[CH3:1][N:2]([CH3:35])[C:3]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=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]([Cl:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 702EthanolHCID 10327255HCID 10327255, compound

Product 1

HCID 103272544-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The polar diastereoisomer of 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (267 mg, 0.54 mmole) was dissolved in abs. ethanol (7 ml). Citric acid (105.1 mg, 0.55 mmole) was added in one portion at ca. 35° C. while stirring. After stirring for several hours at RT no precipitate was visible. The reaction mixture was reduced to ca. 1 ml of solution and diethyl ether (25 ml) was added in portions. The precipitate formed was filtered off after 18 hours, washed with Et2O (3×2 ml) and dried in vacuo. The polar citrate of 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (324 mg, m.p. 125°-130° C., 88%, Example 19) was a colourless solid.

Workup

  1. stirringAfter stirring for several hours at RT no precipitate
  2. additionwas added in portions
  3. customThe precipitate formed
  4. filtrationwas filtered off after 18 hours
  5. washwashed with Et2O (3×2 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-aac63e54445d440282c3c4ae1d405456
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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