(-)-Epichlorohydrin → (r)-1-Chloro-3-(4-methylsulfonyl-1-piperazinyl)-2-propanol

Participants

Reaction Steps

(R)-Epichlorohydrin (3.10 mL, 39.5 mmol) was added to a stirred solution of piperazine sulfonamide trifluoroacetic acid (10.0 g, 35.9 mmol) and NN-diisopropyl-ethylamine (6.26 mL, 35.9 mmol) in ethanol (150 mL) at room temperature. The reaction mixture was stirred for 18 h and a further amount of (R)-epichlorohydrin was added (0.28 mL, 3.6 mmoL) and stirred for an additional 3 h. The reaction mixture was concentrated under vacuum and the white solid was suspended in ethanol (150 mL) and stirred for 2 days. The solid was collected by filtration and washed with cold ethanol to yield (R)-1-chloro-3-(4-methylsulfonyl-1-piperazinyl)-2-propanol (5.69 g) as a white solid which was used without further purification. (m/z): [M+H]+ calcd for C8H17ClN2O3S, 257.07; found 257.2. 1H-NMR (DMSO-d6): δ (ppm) 2.37 (dd, 1H), 2.45 (dd, 1H), 2.50-2.58 (m, 4H), 2.86 (s, 3H), 3.09 (m, 4H), 3.55 (dd, 1H), 3.65 (dd, 1H), 3.84 (m, 1H), 5.09 (d, 1H).

Provenance & Evidence