Triethylamine → 1-[5-(Benzyloxy)pyridin-2-yl]-4-(methanesulfonyl)piperazine

Participants

Reaction Steps

A stirred solution of 1-[5-(benzyloxy)pyridin-2-yl]piperazine (104 g, 278 mmol) in CH2Cl2 (1.1L) at 0° C. was treated sequentially with triethylamine (94 mL, 672 mmol) and methanesulfonyl chloride (31 mL, 400 mmol). The reaction was brought to room temperature and stirred for 3 hour. The reaction was then diluted with DCM (3L) and washed with water (1L), HCl (0.5 M, 2×800 mL) and sat. NaHCO3 (800 mL), back-extracting with DCM (500 mL). The combined organic extracts were then dried (MgSO4), filtered and concentrated in vacuo to give 1-[5-(benzyloxy)pyridin-2-yl]-4-(methylsulfonyl)piperazine as a dark liquor (120 g, 278 mmol @ 81 wt %, 100%).

Provenance & Evidence