Pyridine → HCID 66938945, compound

Participants

Reaction Steps

Combine 1-methyl-4-(N-(3-aminophenyl)-N-methylamino)piperidine (Preparation 11, 101 mg, 0.307 mmol), dichloromethane (6 mL) and pyridine (0.125 mL, 1.535 mmol) at 0° C. Add 2,6-difluorobenzoyl chloride (0.048 mL, 0.384 mmol) neat and continue stirring for 1 hr. Dilute with dichloromethane (5 mL) and wash with sodium hydroxide (1N aq., 2×8 mL). Combine the organic layers, dry over magnesium sulphate, filter under reduced pressure and concentrate to dryness. Purify by flash chromatography, eluting with a 20/1 mixture of dichloromethane/(2N ammonia in methanol) to give the free base of the title compound (88 mg, 80%). Following a salt formation method similar to that described in Example 1 gives the title compound as a yellow solid (89 mg): mass spectrum (free base, ion spray): m/z=360.1 (M+1), 1H NMR (free base, CDCl3): 7.56 (bs, 1H), 7.44–7.34 (m, 2H), 7.20 (t, J=8.2 Hz, 1H), 7.00 (t, J=8.2 Hz, 2H), 6.78 (d, J=8.0 Hz, 1H), 6.59 (dd, J=2.2 Hz, 8.2 Hz, 1H), 3.71–3.63 (bm, 1H), 3.14–3.04 (bm, 2H), 2.82 (s, 3H), 2.41 (bs, 3H), 2.11–1.97 (bm, 2H), 1.79 (bd, J=13 Hz, 2H).

Provenance & Evidence