Sodium Hydroxide → 1-Phenyl-cyclopropylamine

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-phenyl-cyclopropanecarboxylic acid (2.5 g, 15.4 mmol) in a mixture of sulfuric acid (12.5 mL) and DCM (25 mL). Add sodium azide (2.3 g, 35.4 mmol) by small portions at ambient temperature. Heat the reaction mixture at 50° C. for 8 h, cool to 0° C. and slowly add 2M aqueous NaOH until pH 11. Extract the reaction mixture with DCM (3×100 mL), combine the organic extracts and dry over anhydrous Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with DCM and DCM/2M ammonia in methanol (9:1) to obtain the title compound as a brown oil (1.1 g, 54%). MS (ES+) m/z: 134 (M+H)+.

Provenance & Evidence