Citric Acid → 1-(4-Dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea citrate

HRID 1394270Notes

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]([CH3:41])[C:16]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:21][CH2:20][CH:19]([NH:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[S:24])[CH2:18][CH2:17]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>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].[CH3:41][N:15]([CH3:14])[C:16]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:21][CH2:20][CH:19]([NH:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[S:24])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 5 °C

Procedure

In order to produce the citrate, the more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea (410 mg, 1 mmole) was dissolved in hot ethanol (15 ml) and combined with a likewise hot solution of citric acid (422 mg, 2.2 mmole) in ethanol (2 ml). After cooling to approx. 5° C., the batch was left to stand for 4 h. The resultant solid was filtered out. The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea citrate was obtained in this manner as a colorless solid (Example 31, melting point: 63-67° C.) in a yield of 588 mg (100%).

Workup

waitthe batch was left
filtrationThe resultant solid was filtered out

Sources & evidence

ORD record: ord-09bc4851c3ba4cbcab402d8c8cb81b84
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348354B2

Reaction notes

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