Triethylamine → 6-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-1-methyl-6-aza-3-azoniaspiro[2.5]octane chloride

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Reaction Conditions

Reaction Steps

Crude compound IV (29.4 g, 0.106 mol) and triethyl amine (16.2 mL, 0.116 mol) are dissolved in CH2Cl2 (150 mL) and to this solution is added a solution of mesyl chloride (8.6 mL, 0.111 mol) in CH2Cl2 (50 mL) under cooling at 5 to 15° C. over 0.5 h. Stirring is continued overnight at ambient temperature resulting in clear red solution. This solution is washed with water (1×100 mL) and 5% aq. NaHCO3 (1×100 mL). Combined aqueous layers were back-washed with CH2Cl2 (2×50 mL). Organic layers are dried with MgSO4 and concentrated to afford V as thick red oil, yield 31.6 g (101%). 1H NMR (CDCl3) δ6.76 (t, J=7.5 Hz, 1H), 6.55 (m, 2H), 4.27 (m, 4H), 4.11 (m, 1H), 3.10 (m, 4H), 2.8-2.64 (m, 5H), 2.54 (dd, J=7.5, 15 Hz, 1H), 1.55 (d, 3H).

Provenance & Evidence