Diethylene Glycol Monoethyl Ether → HCID 13520603, compound

HRID 1657008Notes

Reaction equation

HRID 1657008 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]#[N:27])[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-].[Na+].C([O:32]CCOCCO)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]([NH2:27])=[O:32])[CH:24]=4)[NH:19][CH:18]=3)[CH2:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8146Diethylene Glycol Monoethyl EtherHCID 14798Sodium HydroxideHCID 13520612HCID 13520612, compound

Product 1

HCID 13520603HCID 13520603, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 35.5 g of 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-butyl]-5-cyanoindole [m.p. 167°; obtainable from the corresponding 5-formyl compound via the oxime], 27.1 g of NaOH, 520 ml of water and 420 ml of diethylene glycol monoethyl ether is stirred for 3 hours at a bath temperature of 140°. The mixture is cooled and worked up in the customary manner to give 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-butyl]-indole-5-carboxamide, m.p. 200°-205°.

Workup

  1. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-10fb7fdbb4dd4b5f8d86570114711e79
Source dataset
uspto-grants-1993_10
Patent number
US05256673

Reaction notes

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