2-(3,4-Dichlorophenoxy)-5-Fluoro-N-Methyl-Benzamide → 1-(2-(3,4-dichlorophenoxy)-5-fluorophenyl)-N-methylmethanamine

Participants

Reaction Steps

Under N2, a mixture of 0.313 g (1.0 mmol) of 2-(3,4-dichlorophenoxy)-5-fluoro-N-methyl-benzamide in 5.0 mL of anhydrous tetrahydrofuran (THF) was treated via syringe with 4.0 mL (4.0 mmol) of 1.0 M BH3 in THF (Aldrich Chem. Co.). and the mixture was heated to reflux for a total of 48 hr. The reaction was quenched by the addition of 25 mL of 6N HCl and heating to reflux until the free amine could be detected by tlc (CHCl3:CH3OH:TEA, (95:5:1)). The cooled mixture was then diluted with water, basified with K2CO3and extracted with EtOAc. The combined organic layers were washed with water and saturated NaCl, then dried with MgSO4, filtered and concentrated in vacuo to the free base as a light brown oil, 0.164 g, 54%). This compound was converted to the hydrochloride salt as described previously, m.p. 200-202°.

Provenance & Evidence