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

HRID 1394280Notes

Reaction equation

HRID 1394280 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 nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]-thiourea (167 mg, 0.37 mmole) was dissolved in ethanol (4 ml) at RT and combined with a solution of citric acid (78.7 mg, 0.41 mmole) in ethanol (1 ml). After 1 h, a tacky precipitate could be seen on the flask wall and was detached mechanically. The batch was then combined with ether (35 ml) and stirred for 20 h. The resultant solid was filtered out, washed with ether (3×3 ml) and dried. The nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]thiourea citrate was obtained in this way as a colorless solid (Example 39) in a yield of 206 mg (87%).

Workup

  1. filtrationThe resultant solid was filtered out
  2. washwashed with ether (3×3 ml)
  3. customdried

Sources & evidence

ORD record
ord-3b76e4d5c374488c8fee4a9af73c889b
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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