N-Methylbenzylamine → 8-(N-Benzyl-N-methylamino)octan-1-ol

Participants

Reaction Conditions

Reaction Steps

8-Bromo-1-octanol (25 g, 119.6 mmol) in ACN (50 mL) was added to a stirred solution of N-benzyl-N-methylamine (43.49 g, 358.9 mmol) and potassium carbonate (49.52 g, 358.9 mmol) in ACN (250 mL) at 35° C. The reaction mixture was then stirred at 35° C. for 7 hours and then cooled to ambient temperature. The potassium carbonate was filtered and the filtrate was concentrated under reduced pressure. The crude residue was dissolved in MTBE (400 mL) and the organic phase was washed with water, brine and dried over magnesium sulfate. N-methyl-2-pyrrolidone was added and the mixture was concentrated under reduced pressure to remove excess N-benzyl-N-methylamine. MTBE (400 mL) was added and the organic phase was washed with water, brine, and dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the title intermediate as an oil (˜100% conversion). MS m/z 250.3 (MH+).

Provenance & Evidence