Water → HCID 70046208, compound

Participants

Reaction Steps

4-Benzyloxybenzoic acid (0.685 g, 3 mmol) was dissolved in DMF (6 ml), and 1,1,-carbonyldiimidazole (0.58 g, 3.6 mmol) was added portionwise. The reaction mixture was heated to 55°-60° C. for 20 min. and then cooled to room temperature. A solution of 1-(2-hydroxy-ethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (0.78 g, 3.3 mmol) in DMF (2 ml) was added. The reaction mixture was stirred 23 hours at room temperature and 4 hours at 60° C. H2O (50 ml) was added followed by CH2Cl2. Organic phase was washed with sat. NaHCO3, dried over Na2SO4, and concentrated. The residue was chromatographed over silica gel (CH2Cl2 --MeOH, 19:1) to provide 4-benzyloxy-benzoic acid 2-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-ethyl ester (0.65 g, 47%) as a colorless solid, m.p. 102° C. and MS: m/e=460.3 (M+H+).

Provenance & Evidence