Methylamine → 11-(Methylamino)undecan-1-ol

Participants

Reaction Steps

A solution of 11-bromoundecanol (25.12 g, 0.10 mol) and methylamine (41% in water, 127 ml, 1.50 mol) in ethanol (50 ml) was heated for 7 h to 70° C. and stirred for a further 16 h at ambient temperature. The solvent was distilled off. After cooling the white solid was dissolved in caustic soda (2N, 200 ml) and diethyl ether (300 ml). The phases were separated and the aqueous phase was extracted with diethyl ether (2×100 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The crude product was recrystallized from diethyl ether. 13.23 g (65.7 mmol, 67% yield) of a while solid (melting point: 58° C.) was obtained.

Provenance & Evidence