HCID 131726477, compound → 2-[2-(Dimethylamino)ethoxy]phenol

Participants

Reaction Steps

To a solution of N-{2-[2-(benzyloxy)phenoxy]ethyl}-N,N-dimethylamine (from Step 1; 7.60 g, 28.0 mmol) in MeOH (80 mL) was added 10% Pd/C (0.8 g) and the mixture was hydrogenated at 70 psi and room temperature for 2 h. The reaction mixture was filtered through a pad of Celite® and silica. The solvent was then removed under reduced pressure to give 5.43 g (quantitative yield) of the title compound as off-white crystals: mp 220° C. HRMS m/z calcd for C10H15NO2 (M)+ 181.1103. Found 181.1105. *The corresponding hydrochloride salt has been reported in Bull. Soc. Chim. Fr. 1935, 1737–1741.

Provenance & Evidence