Diethylene Glycol Monoethyl Ether → Carmoxirole

HRID 1657019Notes

Reaction equation

HRID 1657019 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26](=[O:28])N)[CH:24]=4)[NH:19][CH:18]=3)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:29].[Na+].C(OCCOCCO)C>O>[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]([OH:28])=[O:29])[CH:24]=4)[NH:19][CH:18]=3)[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8146Diethylene Glycol Monoethyl EtherHCID 14798Sodium HydroxideHCID 13520603HCID 13520603, compound

Product 1

HCID 57364Carmoxirole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 37.3 g of 3-[4-(4-phenyl-1,2,3,6tetrahydropyridyl)-butyl]-5-carbamoylindole, 27.1 g of NaOH, 525 ml of water and 450 ml of diethylene glycol monoethyl ether is boiled with stirring for 16 hours. The mixture is cooled, worked up in the customary manner and acidified to give 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-butyl]-indole-5-carboxylic acid, m.p. 284°-285°.

Workup

  1. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-7fb87084acef4a78b9823ff3d483ef9c
Source dataset
uspto-grants-1993_10
Patent number
US05256673

Reaction notes

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