Acetic Acid → HCID 71811815, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 510 mg (2.49 mmol) of 1-[2-(cyclopent-1-en-1-yl)-5-fluorophenyl]ethanone in 5 mL of methanol is added 0.5 g of 3 Å molecular sieves followed by addition of 285 mg (5 mmol) of cyclopropylamine and 375 mg (6.24 mmol) of acetic acid. The reaction mixture is stirred for 90 min at reflux. The reaction mixture is then cooled to 0° C. and 235 mg (3.74 mmol) of sodium cyanoborohydride are slowly added. The reaction mixture is further stirred for 2 hours at reflux. The cooled reaction mixture is filtered over a cake of diatomaceous earth and the cake is washed by ethyl acetate. The aqueous phase is extracted by ethyl acetate and the combined organic extracts are washed by a 1N aqueous solution of sodium hydroxide followed by a saturated aqueous solution of NaCl and dried over a ChemElut™ cartridge. Vacuum concentration yields 810 mg of crude N-{1-[2-(cyclopent-1-en-1-yl)-5-fluorophenyl]ethyl}cyclopropanamine as a brown oil used as such in the next step: (M+H)=246.

Provenance & Evidence