N,N-dimethylheptanamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethylchloroformate (18.3 ml) was added slowly to a solution of heptanoic acid (20.0 g) and triethylamine (26.7 ml) in tetrahydrofuran (250 ml), maintained at -10°. The resulting mixture was stirred at 10° for 0.75 hour, cooled to 5° and a 33% solution of dimethylamine in ethanol (41.6 ml) added dropwise. This mixture was then allowed to warm to room temperature and stirred for 4 hours. The mixture was filtered and the filtrate evaporated to dryness. The residue was dissolved in chloroform (250 ml) and washed with 1% aqueous sodium carbonate solution (200 ml) and water, then dried and evaporated. The residual oil was chromatographed on silica gel to give N,N-dimethylheptanamide (14.1 g) as a colourless oil. maintained at -10° cooled to 5° stirred for 4 hours The mixture was filtered the filtrate evaporated to dryness The residue was dissolved in chloroform (250 ml) washed with 1% aqueous sodium carbonate solution (200 ml) and water dried evaporated The residual oil was chromatographed on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethylchloroformate (18.3 ml) was added slowly to a solution of heptanoic acid (20.0 g) and triethylamine (26.7 ml) in tetrahydrofuran (250 ml), maintained at -10°. The resulting mixture was stirred at 10° for 0.75 hour, cooled to 5° and a 33% solution of dimethylamine in ethanol (41.6 ml) added dropwise. This mixture was then allowed to warm to room temperature and stirred for 4 hours. The mixture was filtered and the filtrate evaporated to dryness. The residue was dissolved in chloroform (250 ml) and washed with 1% aqueous sodium carbonate solution (200 ml) and water, then dried and evaporated. The residual oil was chromatographed on silica gel to give N,N-dimethylheptanamide (14.1 g) as a colourless oil. maintained at -10° cooled to 5° stirred for 4 hours The mixture was filtered the filtrate evaporated to dryness The residue was dissolved in chloroform (250 ml) washed with 1% aqueous sodium carbonate solution (200 ml) and water dried evaporated The residual oil was chromatographed on silica gel