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

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 34.6 g (92% yield) of the crude product as a yellow oil which crystallized on standing: 1H NMR (CDCl3) δ 1.68 (br s, 4 H), 2.51 (m, 2 H), 2.79 (m, 2 H), 2.95 (m, 1 H), 7.24 (m, 5 H).

1. temperatureThe mixture was refluxed for 7.5 h
2. customquenched by the dropwise addition of H2O (200 ml)
3. temperaturewhile cooling in an ice bath
4. filtrationThe solid was filtered
5. washwashed with hot THF (2×500 ml)
6. customthe solvent was removed in vacuo
7. dissolutionThe resulting yellow oil was dissolved in CHCl3
8. filtrationthe solution was filtered
9. dry with materialdried (MgSO4)
10. customThe solvent was removed in vacuo

ORD record

ord-df35120f189144eb850b49f57922816b

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05874421