Chloroacetaldehyde → HCID 67064917, compound

Participants

Reaction Conditions

Reaction Steps

The (trans)-2-phenylcyclopropanamine previously obtained was added to activated and dried molecular sieves (3 A), proceeding with several vacuum and argon cycles. DCM (120 mL) was added and stirred before adding chloroacetaldehyde (1.5 mL, 12.0 mmol) and stirring for 4 hours. The reaction was cooled to 0° C. and NaBH3CN (0.88 g, 14.0 mmol) was added. The mixture was stirred at room temperature overnight. NH4Cl (20 mL) was added and the organic layer was extracted, dried with MgSO4 and filtered. The crude was purified by silica gel chromatography (Hexane-MTBE 70:30) affording 1.68 g (8.56 mmol) of N-(2-chloroethyl)-N-[(trans)-2-phenylcyclopropyl]amine. Yield: 72%. 1HNMR (CDCl3) δ (ppm): 1.01 (q, 1H), 1.08 (quin, 1H), 1.93 (m, 1H), 2.37 (quin, 1H), 3.08 (t, 2H), 3.67 (t, 2H), 7.04 (d, 2H), 7.15 (t, 1H), 7.25 (t, 2H). MS (M+H): 195.88

Provenance & Evidence