Methanesulfonyl chloride → (S)-2-Benzyl-4-(3-cyclopentyloxy4-methoxy-phenyl)-1-methanesulfonyl-piperazine

Participants

Reaction Steps

A solution of the bis-hydrochloride salt of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (50 mg, 0.114 mmol) in pyridine (1 mL) was treated with methanesulfonyl chloride (26 μL, 0.341 mmol) and stirred at room temperature for 16 h. The reaction mixture was evaporated and partitioned between EtOAc (2 mL) and a saturated aqueous NaHCO3 solution (2 mL). The organic component was separated, dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 30% then 40% EtOAc/hexane as eluant to afford product as an oil (46 mg, 91%). 1H NMR (CDCl3) 1.60-1.62 (M, 2H), 1.84-1.87 (m, 4H), 1.90-2.04 (m, 2H), 2.55 (s, 3H), 2.76-2.80 (m, 2H), 3.19-3.56 (m, 5H), 3.77 (m, 1H), 3.80 (s, 3H), 4.30 (br t, 1H), 4.71 (m, 1H), 6.42 (br d, J=8.1, 1H), 6.48 (br s, 1H), 6.78 (d, J=8.6, 1H), 7.23-7.36 (m, 5H). LC/MS 7.25 min, [M+1]+ 445.

Provenance & Evidence