Water → N-methyl-N-(2-cycloheptenyl)benzamide

HRID 247617

Reaction equation

HRID 247617 reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH:14]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH:15]1.O>CN(C)C=O>[CH3:3][N:4]([CH:20]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1)[C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11954N-MethylbenzamideHCID 24758Sodium hydrideHCID 124538813-Bromocyclohept-1-ene

Product 1

HCID 13647212N-methyl-N-(2-cycloheptenyl)benzamideYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension (10 ml) of sodium hydride (0.24 g, 10 mmoles) in dimethylformamide was added dropwise at 0° C. a dimethylformamide solution (1 ml) of N-methylbenzamide (1.35 g, 10 mmoles). After completion of the addition, the temperature was raised to room temperature, and after stirring for 15 minutes, 3-bromocycloheptene (1.75 g, 10 mmoles) was added dropwise. The resulting mixture was stirred at room temperature for 24 hours, poured into water (20 ml) and extracted with ether. The oily product obtained by concentration was purified by chromatography on silica gel to obtain 0.92 g of N-methyl-N-(2-cycloheptenyl)benzamide [Compound (54)].

Workup

  1. additionAfter completion of the addition
  2. stirringThe resulting mixture was stirred at room temperature for 24 hours
  3. extractionextracted with ether
  4. customThe oily product obtained by concentration
  5. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ee9b15d511d74dd388ddac7cf41b144c
Source dataset
uspto-grants-1987_11
Patent number
US04709052

Linked notes

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