Phenylalaninamide--hydrogen chloride (1/1) → 3-Phenylpropane-1,2-diamine

Participants

Reaction Steps

To a stirred slurry of D,L-phenylalanine amide hydrochloride (50.0 g, 0.249 mole) in anhydrous THF (200 ml) at room temperature under a dry argon atmosphere was added a solution of lithium aluminum hydride (1000 ml-1.0M in THF, 1.00 mole) over a 30 minute period. The mixture was refluxed for 7.5 h and then quenched by the dropwise addition of H2O (200 ml) while cooling in an ice bath. The solid was filtered, washed with hot THF (2×500 ml) and then hot methanol (2×500 ml). The filtrate and washings were combined and the solvent was removed in vacuo. The resulting yellow oil was dissolved in CHCl3 and the solution was filtered and dried (MgSO4). The solvent was removed in vacuo to give 34.6g (92% yield) of the crude product as a yellow oil which crystallized on standing: 1H NMR (CDCl3) δ1.68 (br s, 4 H), 2.51 (m, 2 H), 2.79 (m, 2 H), 2.95 (m, 1 H), 7.24 (m, 5 H).

Provenance & Evidence