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

HRID 2357486Notes

Reaction equation

HRID 2357486 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][CH2:16][CH:15]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[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: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][CH2:16][CH:15]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:14]2)=[O:12])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 702EthanolHCID 593855623-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide

Product 1

HCID 675309973-(5-fluoro-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 3-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (115 mg, 0.241 mmole) was dissolved in abs. ethanol (1.5 ml). Citric acid (46.8 mg, 0.244 mmole) was added in one portion at ca. 40° C. while stirring. No precipitate formed at RT. Diethyl ether (50 ml) was slowly added to the reaction solution. The resulting suspension was stirred for 1 hour at RT. The precipitate was filtered off, washed with diethyl ether (3×2 ml) and dried in vacuo. The polar diastereoisomer of 3-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate (133 mg, m.p. 128°-130° C., 83%, Example 50) was a colourless solid.

Workup

  1. customNo precipitate formed at RT
  2. stirringThe resulting suspension was stirred for 1 hour at RT
  3. filtrationThe precipitate was filtered off
  4. washwashed with diethyl ether (3×2 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-584358be57804929b7a11586d7a60760
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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