Acetic Acid → (4-Fluoro-benzyl)-{3-[(4-fluoro-benzylamino)-methyl]-benzyl}-amine

Participants

Reaction Steps

To a partially heterogeneous mixture of N1,N3-bis(4-fluorobenzyl)isophthalamide (5.1 g, 13.41 mmol) in THF (70 mL) at ice bath temp was added a cold solution of borane (100 mL of 1 M solution in THF) slowly. It was stirred at ice bath tem for 1 h. It was warmed to rt and stirred for 30 h at rt. The mixture was warmed to ˜60° C. and stirred for 2 h. To the mixture was added 5 mL of HOAc, stirred for 1 h and it was mostly concentrated. To the residue was slowly added 150 mL of MeOH and 150 mL of 1N HCl with stirring, stirred for 2 h at rt, heated at 65° C. for 30 min and it was mostly concentrated. The mixture was mixed with EtOAc and aq NaHCO3, the EtOAc layer was separated, washed with water, dried over MgSO4 and concentrated in vacuo to obtain the desired product (4.5 g, 95%) as a viscous material of crude product. This crude product was used directly for the next step without any further purification.

Provenance & Evidence