N,1-diphenylethan-1-imine → N-(1-Phenylethyl)aniline

Participants

Reaction Conditions

Reaction Steps

The reaction was carried out in a multiwell hydrogenation vessel. Dichloro-{1,2-Bis[(2R,5R)-2,5-diphenylphospholano]methane}[(1S,2S)-1,2-diphenylethylenediamine)] ruthenium (II) (2.2 mg, 0.0025 mmol) was suspended in degassed isopropanol (2 ml) in a Schlenk flask under nitrogen. Added potassium tert-butoxide (1M in tert-butanol, 0.025 ml) and heated until a yellow solution was obtained. The glass liner was charged with N-(1-phenylethylidene)aniline (98 mg, 0.50 mmol). Charged to 10 bar nitrogen and vented (×5). Added the precatalyst solution and charged to 10 bar nitrogen and vented (×2). Commenced stirring at 1000 rpm and heated to 60° C. Charged to 10 bar H2 and stirred for 18 h. Cooled to room temperature, vented and evaporated to give phenyl-(1-phenylethyl)amine, conversion>99%, ee 71% (GC, sample derivatised by treatment with acetic anhydride pyridine, Chirasil DEX CB, 25 m×0.25 mm, injector/detector 200° C., helium 20 psi, 140° C. for 20 minutes then ramp at 5° C./min to 200° C., hold for 5 minutes, retention times 23.21 minutes and 23.45 minutes).

Provenance & Evidence