Pyrrolidine → 1-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}pyrrolidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(bromomethyl)-7-(methylsulfonyl)-4H-1,3-benzodioxine (0.5 g, 1.63 mmol), pyrrolidine (2.0 ml, 24.0 mmol) and EtOH (4.0 ml) was heated in a micro wave oven at 130° C. for 30 min. The mixture was evaporated to dryness. The residue was chromathographed on a silica column using EtOAc/MeOH (10:1) as eluent, affording the title compound (0.37 g, 76%). The title compound (0.26 g) was converted into the hydrochloric acid salt and crystallized from EtOH/DEE. M.p. 199° C. 1H-NMR (400 MHz, MeOH): δ 7.49 (1H, dd, J 18 Hz, J 21.6 Hz), δ 7.40 (1H, d, J 1.6 Hz), δ 7.31 (1H, d, J 8 Hz), 5.29 (1H, t, J 4.4 Hz), δ 5.03 (2H, dd, J 56 Hz, 16 Hz), δ 3.1 (3H, s), 2.92 (2H, m), δ 2.70 (4H, m), δ 1.83 (4H, m).

Provenance & Evidence