Borane;tetrahydrofuran → N-benzyl-N'-(4-fluoro-2-methyl-phenyl)-ethane-1,2-diamine

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Reaction Steps

To a solution of N-benzyl-2-(4-fluoro-2-methyl-phenylamino)-acetamide (17 g) in THF (500 mL) was added a solution of borane tetrahydrofuran complex (499.4 mL, 1M in THF). The solution was heated to reflux for 4 h, was concentrated and redissolved in a mixture of 2M HCl and TBME. The inorganic phase was extracted with TBME, the organic phases washed with 2M HCl. The pH of the combined inorganic phases was adjusted to pH 11 by the addition of concentrated NaOH, and the solution was extracted with TBME. The combined organic phases were dried (Na2SO4), filtered and evaporated to yield N-benzyl-N′-(4-fluoro-2-methyl-phenyl)-ethane-1,2-diamine (15.1 g) as a crude product, MS: 259.3 ([M+H]+).

Provenance & Evidence