Citric Acid → HCID 9986926, compound

HRID 2357480Notes

Reaction equation

HRID 2357480 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][CH:17]=[C:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:5][CH2:4]1.[C:36]([OH:48])(=[O:47])[CH2:37][C:38]([CH2:43][C:44]([OH:46])=[O:45])([C:40]([OH:42])=[O:41])[OH:39]>C(O)C>[C:36]([OH:48])(=[O:47])[CH2:37][C:38]([CH2:43][C:44]([OH:46])=[O:45])([C:40]([OH:42])=[O:41])[OH:39].[CH3:1][N:2]([CH3:35])[C:3]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:4][CH2:5][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:14][CH:15]=[C:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 311Citric Acid2×HCID 9986927HCID 9986927, compound

Product 1

HCID 9986926HCID 9986926, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The polar diastereoisomer of 4-(5-fluoro-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl-methyl)-amide (140 mg, 0.294 mmole) was dissolved in abs. ethanol (10 ml). Citric acid (105.7 mg, 0.55 mmole) was added in solid form. The mixture was stirred at 40° C. until the citric acid had completely dissolved. A sticky precipitate formed at RT on the wall of the flask. The alcohol was distilled off and the residue was dried in vacuo. The polar diastereoisomer of 4-(5-fluoro-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl-methyl)-amide citrate (255 mg, hygroscopic, Example 44) was an orange-brown solid.

Workup

  1. dissolutionhad completely dissolved
  2. customA sticky precipitate formed at RT on the wall of the flask
  3. distillationThe alcohol was distilled off
  4. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-17357358d1704047bf3a7138e5e8cb6e
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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