Phenylacetaldehyde → 2-Amino-3-phenylpropanenitrile

Participants

Reaction Conditions

Reaction Steps

In a 1L 5-necked flask equipped with a mechanical stirrer, thermometer, condenser and a dropping funnel was placed potassium cyanide (71.5 g, 1.1 mol) in water (325 mL). Ammonium chloride (64.2 g, 1.2 mol) was added. The resulting mixture was stirred to get a homogenous solution. A solution of phenylacetaldehyde (132 g of 90% purity, 1.0 mol) in methanol (325 mL) was added over 60 min. The resulting mixture was heated at 60° C. HPLC analysis indicated that the reaction was complete after 4 hr. The reaction mixture was cooled to room temperature and then dichloromethane (250 mL) and water (259 mL) were added. The aqueous layer was separated and extracted with dichloromethane (250 mL). The combined organic layers were washed with water (1×100 mL), and product was extracted with 2N HCl (2×300 mL). The combined acidic layers were back washed with dichloromethane (1×250 mL). Dichloromethane (250 mL) was added to the aqueous acidic layer after which the mixture was cooled in an ice-water bath and basified with concentrated ammonia (150 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×100 ml). The organic layers were combined and washed with water (1×100 mL) then with brine (1×100 mL) and dried over anhydrous magnesium sulfate (15 g). The magnesium sulfate was filtered and the solution was evaporated under reduced pressure to give 80 g (55% yield) of the aminonitrile 2 as an oil. The oil solidified on standing in the refrigerator overnight. HPLC analysis showed a purity of 99%. NMR (CDCl3) δ 7.5 (s, 5H), 3.7–4.1 (m, 1H), 3.05 (d, 2H), 1.7 (s br, 2H).

Provenance & Evidence