Triethylamine → HCID 806418, compound

Participants

Reaction Steps

4-Bromobenzyl bromide (0.5 g, 2.0 mmol) was stirred with 4-piperidin-4-yl-morpholine (0.67 g, 4.0 mmol) and triethylamine (0.42 mL, 3.0 mmol) in THF (20 mL) at ambient temperature for 28 h then a further 1.5 eq of triethylamine was added and stirring continued for 16 h. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The resultant residue was purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in cyclohexane then 0-10% (2N ammonia in methanol) in DCM) to afford the title compound as an off-white solid (0.62 g, 92%). 1H NMR (CDCl3, 400 MHz): 7.44-7.40 (m, 2H), 7.21-7.15 (m, 2H), 3.74-3.69 (m, 4H), 3.42 (s, 2H), 2.93-2.85 (m, 2H), 2.56-2.50 (m, 4H), 2.22-2.13 (m, 1H), 2.00-1.91 (m, 2H), 1.82-1.74 (m, 2H), 1.59-1.47 (m, 2H).

Provenance & Evidence