Methyl iodide → N,N-dibenzyl-2-(1-methoxycyclopropyl)ethanamine

Participants

Reaction Steps

Treat a 0° C. solution of 1-(2-(dibenzylamino)ethyl)cyclopropanol (3 g, 10.6 mmol) in THF (50 mL), under N2, portion wise with NaH (60%, 0.85 g, 21.3 mmol), stir at 0° C. for 0.5 h, add iodomethane (1.82 g, 12.8 mmol) drop wise, warm to RT and stir for 3 h. Cool the mixture to 0° C., quench with satd. NH4Cl and partially concentrate. Extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (1.2 g, 38%). 1H NMR (400 MHz, CDCl3): δ 7.39-7.21 (m, 10H), 3.60 (s, 4H), 3.12 (s, 3H), 2.65 (t, J=8 Hz, 2H), 1.75 (t, J=8 Hz, 2H), 0.68-0.65 (m, 2H), 0.34-0.31 (m, 2H).

Provenance & Evidence