1-Phenylcyclopropanecarbonitrile → 1-Phenylcyclopropanemethanamine

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Reaction Steps

LiAlH4 (1.8 g, 48 mmol) is added in batches over 5 min to a solution of 1-phenylcyclopropane carbonitrile (6.58 g, 46 mmol) in ether (200 mL) stirred under N2 at 0°. After 1 h the reaction mixture is quenched by a careful dropwise addition of water (1.8 mL), 10% W/V NaOH solution (1.8 mL) and water (5.4 mL). Vigorous gas evolution again occurs. The mixture is vacuum filtered, and the filtrate is extracted with dilute HCl (0.2M, 3×100 mL). The combined extracts are washed with ether (3×100 mL) and made basic with NaOH pellets (3.2 g, 80 mmol). The aqueous layer is extracted with ether (3×100 mL). The combined organic phases are washed with water (2×100 mL), saturated brine (100 mL) and dried (MgSO4). The solvent is removed under reduced pressure to give (1-phenylcyclopropyl)methylamine (4.98 g, 74%) as an orange oil. Nmr δ (CDCl3) 7.1-7.5 (5H, m), 2.77 (2H, S), 1.3 (2H, br s), 0.6-0.95 (4H, m).

Provenance & Evidence