Citric Acid → HCID 10009134, compound

HRID 1394278Notes

Reaction equation

HRID 1394278 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]([CH2:22][NH:23][C:24]([NH:26][CH2:27][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].[CH3:44][N:15]([CH3:14])[C:16]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][C:24]([NH:26][CH2:27][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 10009135HCID 10009135, compound

Product 1

HCID 10009134HCID 10009134, compound

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)ethyl]thiourea (253 mg, 0.582 mmole) was dissolved in ethanol (4 ml) at RT and combined with a solution of citric acid (123 mg, 0.588 mmole) in ethanol (1 ml). After 2 h, the batch was combined with 20 ml ether and stirred for 18 h. The resultant solid was filtered out, washed with ether (3×2 ml) and dried. The nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)ethyl]-thiourea citrate could be obtained in this manner as a light yellow solid in a yield of 297 mg (Example 37, 81%).

Workup

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

Sources & evidence

ORD record
ord-2fc9e556b16b4ff7b2f04208d801f1b4
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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