Dimethylamine → N,N-dimethyl-4-(4-oxocyclohexyl)benzamide

HRID 567394Notes

Reaction equation

HRID 567394 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C1(C2CCC(=O)CC2)C=CC=CC=1.[CH3:30][NH:31][CH3:32]>>[CH3:30][N:31]([CH3:32])[C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:8]([CH:5]2[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]2)=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 786054-PhenylcyclohexanoneHCID 109774594-(4-oxocyclohexyl)benzoyl Chloride

Product 1

HCID 11107611N,N-dimethyl-4-(4-oxocyclohexyl)benzamideYield 68%

Procedure

4-(4-Oxocyclohexyl)benzoyl chloride [obtainable by reacting 0.75 mol (130.7 g) of 4-phenylcyclohexanone with 1 mol of oxalyl chloride and 2 mol of AlCl3 in dichloromethane, followed by hydrolysis with ice-water/HCl] is added to an aqueous solution (15%) of 3 mol of dimethylamine and the mixture is stirred for 2 hours at 0 to 5°. It is worked up in conventional manner to give 125.2 g of N,N-dimethyl-4-(4-oxocyclohexyl)benzamide, m.p. 118°; yield: 68% based on 4-phenylcyclohexanone.

Sources & evidence

ORD record
ord-bb5184ef78fc40c2b21110094bd0e882
Source dataset
uspto-grants-2001_01
Patent number
US06177594B1

Reaction notes

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