Citric Acid → 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]thiourea citrate

HRID 1394281Notes

Reaction equation

HRID 1394281 reaction equation
[C:1]([O-:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([O-:11])=[O:10])([C:5]([O-:7])=[O:6])[OH:4].[CH3:14][N:15]([CH3:45])[C:16]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][C:24]([NH:26][CH:27]([CH3:38])[CH2:28][C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:31][CH:30]=2)=[S:25])[CH2:18][CH2:17]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.CCOCC>C(O)C>[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH3:45][N:15]([CH3:14])[C:16]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][C:24]([NH:26][CH:27]([CH3:38])[CH2:28][C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:31][CH:30]=2)=[S:25])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 3283Diethyl EtherHCID 31348CitrateHCID 596818901-(4-Dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]thiourea

Product 1

HCID 866017961-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]thiourea citrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In order to produce the citrate, the more polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]-thiourea (140 mg, 0.31 mmole) was dissolved in ethanol (4 ml) and combined with a solution of citric acid (65.9 mg, 0.34 mmole) in ethanol (1 ml). Only a little precipitate formed. The mixture was thus combined with ether (50 ml). After 20 h stirring at RT, the resultant solid was filtered out. The more polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]thiourea citrate was obtained in this manner as a colorless solid (Example 40) in a yield of 185.5 mg (93%).

Workup

  1. customOnly a little precipitate formed
  2. filtrationthe resultant solid was filtered out

Sources & evidence

ORD record
ord-d40ba43f2c104cdb9b6581e60143dc34
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

Loading…