1,2-Dichloroethane → 2,4-Difluoro-N-(3-(1-methylpiperidin-4-ylamino)-4-fluorophenyl)benzamide hydrochloride

Participants

Reaction Steps

Using a procedure similar Example 24 using 2,4-difluoro-N-(3-amino-4-fluorophenyl)benzamide (Preparation 16, 452 mg, 1.7 mmol), 1-methyl-4-piperidone (384 mg, 0.42 mL, 3.4 mmol), 1,2-dichloroethane (15 mL), powdered molecular sieves 4 Å (1 g), glacial acetic acid (306 mg, 0.3 mL, 5.1 mmol), sodium triacetoxyborohydride (900 mg, 4.25 mmol) to obtain the free base of the title compound (434 mg, 70% yield) and the title compound: mass spectrum (ion spray): m/z=364.1 (M+1); analysis calculated for C19H20F3N3O.HCl.H2O: C, 54.61; H, 5.55; N, 10.06. Found: C, 54.48; H, 5.36; N, 9.93; 1H NMR δ (methanol-d4) 7.79 (m, 1H), 7.63 (d, 1H), 7.11 (m, 4H), 3.74 (m, 1H), 3.62 (d, 2H), 3.30 (dd, 2H), 2.88 (s, 3H), 2.36 (d, 2H), 1.93 (m, 2H)

Provenance & Evidence