Citric Acid → HCID 24956142, compound

HRID 1095565Notes

Reaction equation

HRID 1095565 reaction equation
[CH2:1]([C:5]1([N:27]([CH3:29])[CH3:28])[CH2:10][CH2:9][CH:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)C.[ClH:48]>C(O)C>[ClH:48].[CH2:1]([C:5]1([N:27]([CH3:28])[CH3:29])[CH2:6][CH2:7][CH:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 24956143HCID 24956143, compound

Product 1

HCID 24956142HCID 24956142, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Butyl-4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine (polar diastereomer) (135 mg, 0.342 mmol) and citric acid (71 mg, 0.370 mmol) were dissolved in hot ethanol (4 ml). Diethyl ether (26 ml) was slowly added dropwise to the clear solution at room temperature. The mixture was stirred at room temperature overnight. The white solid was filtered off and washed with diethyl ether. was obtained in a yield of 50% (101 mg) with a melting point of 268-272° C. This product was identified as the hydrochloride.

Workup

  1. filtrationThe white solid was filtered off
  2. washwashed with diethyl ether
  3. customwas obtained in a yield of 50% (101 mg) with a melting point of 268-272° C

Sources & evidence

ORD record
ord-50b84956c0b54057a9cb35c286f3083c
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…