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

HRID 2357448Notes

Reaction equation

HRID 2357448 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][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:5][CH2:4]1.C(O)C.[C:38]([OH:50])(=[O:49])[CH2:39][C:40]([CH2:45][C:46]([OH:48])=[O:47])([C:42]([OH:44])=[O:43])[OH:41]>C(Cl)Cl>[C:38]([OH:50])(=[O:49])[CH2:39][C:40]([CH2:45][C:46]([OH:48])=[O:47])([C:42]([OH:44])=[O:43])[OH:41].[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[CH2:14][CH2:15][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:5][CH2:4]1.[NH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([C:11]([NH:10][CH2:9][CH:6]3[CH2:7][CH2:8][C:3]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([N:2]([CH3:1])[CH3:34])[CH2:4][CH2:5]3)=[O:12])[CH2:14][CH2:15]2)=[CH:20]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 702EthanolHCID 10416821HCID 10416821, compound

Product 1

HCID 1317282564-(1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide hemicitrateYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The non-polar diastereoisomer of 4-(1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (280 mg, 0.61 mmole) was dissolved in abs. ethanol (16 ml) and DCM (6 ml). Citric acid (118 mg, 0.616 mmole) was added in one portion at ca. 40° C. while stirring. After 20 minutes a colourless precipitate began to form. The suspension was stirred for 24 hours at RT. Following this the precipitate was filtered off and washed with cold ethanol (2×1 ml) and diethyl ether (4×2 ml). The non-polar diastereoisomer of 4-(1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide hemicitrate (241 mg, m.p. 165°-168° C., 61%, Example 16) was obtained as a colourless solid.

Workup

  1. customto form
  2. stirringThe suspension was stirred for 24 hours at RT
  3. filtrationwas filtered off
  4. washwashed with cold ethanol (2×1 ml) and diethyl ether (4×2 ml)

Sources & evidence

ORD record
ord-339fcaea7f88444da10fce93263e7efb
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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