Potassium Hydroxide → Carmoxirole

HRID 1657009Notes

Reaction equation

HRID 1657009 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([O:21]C)=[O:20])=[CH:16][CH:17]=3)[C:12]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:32][CH:31]=[C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:29][CH2:28]3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[K+]>O.C(O)C>[C:33]1([C:30]2[CH2:31][CH2:32][N:27]([CH2:26][CH2:25][CH2:24][CH2:23][C:12]3[C:13]4[C:18](=[CH:17][CH:16]=[C:15]([C:19]([OH:21])=[O:20])[CH:14]=4)[NH:10][CH:11]=3)[CH2:28][CH:29]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57308379HCID 57308379, compound

Product 1

HCID 57364Carmoxirole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4.68 g of methyl 1-benzenesulfonyl-3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-butyl]-indole-5-carboxylate [obtainable from methyl 1-benzenesulfonyl-3-(4-chlorobutyl)-indole-5-carboxylate and 4-phenyl-1,2,3,6-tetrahydropyridine] are boiled with 1 g of KOH in 7 ml of water and 14 ml of ethanol for 16 hours, and the mixture is concentrated and worked up in the customary manner to give 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-butyl]-indole-5-carboxylic acid, m.p. 284°-285°.

Workup

  1. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-a5f4899dda9443edabcc7b37411fa071
Source dataset
uspto-grants-1993_10
Patent number
US05256673

Reaction notes

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