Citric Acid → HCID 86601799, compound

HRID 1394288Notes

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][CH2:23][NH:24][C:25]([NH:27][CH2:28][CH2:29][C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][CH:31]=2)=[S:26])[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].[CH3:45][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][CH2:23][NH:24][C:25]([NH:27][CH2:28][CH2:29][C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][CH:31]=2)=[S:26])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 5 °C

Procedure

In order to produce the citrate, the more polar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)ethyl]-3-[2-(1H-indol-3-yl)ethyl]thiourea (330 mg, 0.71 mmole) was dissolved in hot ethanol (4 ml) and combined with a likewise hot solution of citric acid (137 mg, 0.71 mmole) in ethanol (1 ml). After cooling to approx. 5° C., the batch was left to stand for 4 h. Since no solid precipitated out, the ethanol was removed by distillation. The more polar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)ethyl]-3-[2-(1H-indol-3-yl)-ethyl]thiourea citrate was obtained in this manner as a colorless foam (Example 44, melting point: 90-95° C.) in a yield of 467 mg (100%).

Workup

waitthe batch was left
customSince no solid precipitated out
customthe ethanol was removed by distillation

Sources & evidence

ORD record: ord-8a17d929c2704fe59c2cc9a50f1d9c7c
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348354B2

Reaction notes

Loading…