3-(Chloromethyl)pyridine hydrochloride → HCID 19708698, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 52 (147 mg, 0.44 mmol), 3-picolylchloride hydrochloride (73 mg, 0.44 mmol and a crystal of KI were combined in DMF (30 ml). Sodium hydride (44 mg, 1.1 mmol, a 60% dispersion in oil) was added and the mixture was stirred at 90° C. for 15 hr. At this time the solvent was evaporated under reduced pressure and the residue was partitioned between 1N aq KOH and CHCl3. The CHCl3 phase was dried (Na2SO4) and concentrated and the residue was purified by flash chromatography using 5% acetone in CHCl3. The pure product was obtained as a tan foam (124 mg, 66% yield): 1H NMR (CDCl3) δ 1.53-1.76 (8H, m, 4×CH2), 2.06 (2H, s, 2×CH), 3.21 (4H, d, J=4.19 Hz, 2×CH2), 5.34 (2H, s, CH2Ar), 7.12 (1H, s, ArH), 7.37 (1H, m, ArH), 7.64 (2H, m, ArH), 7.82-7.98 (3H, m, ArH), 8.35 (1H, m, ArH), 8.62 (1H, m, ArH), 8.80 (1H, m, ArH).

Provenance & Evidence