Dimethylamine → HCID 22638783, compound

Participants

Reaction Steps

Trans-2-benzo[b]thiophen-3-yl-cyclopropanecarbaldehyde (202 mg, 1.0 mmol) was dissolved in 10 mL ethanol. To this solution was added a 2.0 M solution of dimethylamine in THF (5.0 mL, 10.0 mmol). After stirring for 15 min, sodium triacetoxyborohydride (850 mg, 4.0 mmol) was added and the reaction continued for 1 h. The reaction was diluted with 10 mL 0.1 N HCl, then solid sodium bicarbonate was added in portions to adjust pH to 7. The mixture was extracted with ethyl acetate (2×20 mL), and the organic extracts were pooled, washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by preparative reverse phase high-performance liquid chromatography afforded (2-benzo[b]thiophen-3-yl-cyclopropylmethyl)-dimethyl-amine (246 mg, 71%) as an oily trifluoroacetic acid salt. 1H NMR (500 MHz, d4-MeOH) 7.94 (1H, d, J=7.94 Hz), 7.86 (1H, d, J=7.93 Hz), 7.42 (1H, t, J=7.94), 7.37 (1H, t, J=7.94), 7.21 (1H, s), 3.44 (1H, dd, J=13.12, 6.71 Hz), 3.22 (1H, dd, J=13.12, 8.24 Hz), 2.97 (6H, s), 2.28 (1H, p, J=4.6 Hz), 1.56 (1H, m), 1.20 (2H, m). LC-MS: 1.10 min; 232.2 (MH)+.

Provenance & Evidence