[C:1]1([CH2:7][CH:8]([NH2:11])[C:9]#[N:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.CC(C[AlH]CC(C)C)C.[OH-].[Na+]>ClCCl>[C:1]1([CH2:7][CH:8]([NH2:11])[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1A solution of 2 (18.25 g, 0.125 mol) in dichloromethane (150 mL) was added over 30 min to a 1M solution diisobutylaluminum hydride of DIBAL (500 mL, 0.5 mol) cooled to −10°. The temperature raised to −5° and returned to −10°. The starting material was gone after 15 min (GC). The cooled reaction mixture was treated with 500 mL of aqueous 2N sodium hydroxide at a rate, which kept the temperature under 20°. The resulting mixture was stirred at room temperature for 1 hr and then it was filtered through 1PS filter paper. The solvent was evaporated under reduced pressure and the residue was distilled through a short path column to give 12.7 g (68% yield) of 3-phenyl-1,2-diamino-propane, 3 (b.p. 78–83° C., 0.2–0.3 mm) which was 90% pure by glpc. NMR (CDCl3) δ 7.4 (s, 5H), 2.4–3.2 (m, 5H), 1.4 (s, 4H).
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