Citric Acid → HCID 86601795, compound

HRID 1394273Notes

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]([CH3:44])[C:16]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:21][CH2:20][CH:19]([NH:22][C:23]([NH:25][CH:26]([CH3:37])[CH2:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][CH:29]=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].[CH3:44][N:15]([CH3:14])[C:16]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:17][CH2:18][CH:19]([NH:22][C:23]([NH:25][CH:26]([CH3:37])[CH2:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][CH:29]=2)=[S:24])[CH2:20][CH2:21]1

Participants

Conditions

Temperature: 5 °C

Procedure

In order to produce the citrate, the more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-thiourea (256 mg, 0.59 mmole) was dissolved in hot ethanol (8 ml) and combined with a likewise hot solution of citric acid (249 mg, 1.3 mmole) in ethanol (1 ml). After cooling to approx. 5° C., the batch was left to stand for 4 h. The resulting solid was filtered out. The more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-thiourea citrate could be obtained in this manner as a colorless solid (Example 34, melting point: 108-113° C.) in a yield of 369 mg (100%).

Workup

waitthe batch was left
filtrationThe resulting solid was filtered out

Sources & evidence

ORD record: ord-d21f6caa31c2497ab2a51629d1dc02d9
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348354B2

Reaction notes

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