N,N-Diethylethylenediamine → N,N-Diethyl-N'-(4'-trifluoromethylbiphenyl-4-ylmethyl)-ethane-1,2-diamine

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Reaction Steps

N,N-diethylethylene diamine (2.50 kg, 21.12 moles) was added to a solution of 4-(4-trifluoromethylphenyl)benzaldehyde (3.54 kg, 14.08 moles) in toluene (21 L) and rinsed in with toluene (14 L) with stirring. The resultant solution was stirred at 17-21° C. for ca. 96 hours. The solution was then transferred to a hydrogenation vessel containing 5% palladium on alumina (0.213 kg, 0.11 moles Pd) and rinsed in with toluene (37 L). The mixture was hydrogenated at 19−27° C., 50 psig hydrogen for 1 hour until no further hydrogen was consumed. The catalyst was removed by filtration through celite (0.5 kg) and the celite bed was washed with toluene (14 L). The combined filtrate and wash were washed with process water (3×14 L) then the toluene removed by distillation at 20-80° C. in vacuo to give the title compound as a pale yellow oil (4.96 kg, 97.3%). 1H NMR (CDCl3) δ 1.01 (6H, t), 2.52 (4H, q), 2.58 (2H, t), 2.70 (2H, t),3.86 (2H, s), 7.42 (2H, d), 7.43 (2H, d), 7.68 (4H, s).

Provenance & Evidence