Cyclohexylamine → 5-Chloro-N-cyclohexylpentanamide

Temperature

0 °C

A stirred solution of 5-chlorovaleryl chloride (50.0 g, 0.322 mol) in dichloromethane (300 ml) at 0° C. was treated dropwise with a solution containing cyclohexylamine (31.68 g, 0.320 mol), triethylamine (32.32 g, 0.320 mol) and dimethylaminopyridine (0.02 g) in dichloromethane (300 ml). The resulting solution was stirred for 2 hours at 0° C. and then for an additional 16 hours at room temperature. The solution was diluted with dichloromethane (400 ml), washed with water (3×200 ml), saturated aqueous sodium hydrogen carbonate (3×100 ml), saturated aqueous ammonium chloride (3×100 ml), and brine (2×100 ml) and then dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure to yield a crude product. The crude product was recrystallized from ethyl acetate-hexane to yield N-cyclohexyl-5-chloropentanamide as a colorless crystalline solid, having a melting point of 70°-71° C. and the following physical characteristics:

1. waitfor an additional 16 hours at room temperature
2. washwashed with water (3×200 ml), saturated aqueous sodium hydrogen carbonate (3×100 ml), saturated aqueous ammonium chloride (3×100 ml), and brine (2×100 ml)
3. dry with materialdried over anhydrous sodium sulfate
4. customThe solvent was evaporated off under reduced pressure
5. customto yield a crude product
6. customThe crude product was recrystallized from ethyl acetate-hexane

ORD record

ord-a5fa354a8be8430e9d9400c4ef7a1c23

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04804658