反应详情

A mixture of 1-benzyl-4-(4-methoxyphenyl)piperidin-4-ol (XIV, Step 1, 8.37 g, 28.1 mmol) and concentrated hydrochloric acid/H2O (1/1, 28 ml) is heated at 76° for 3 min. The resulting slurry is cooled and aqueous sodium hydroxide is added to make the mixture basic. The mixture is extracted several times with dichloromethane and the combined organic extracts are backwashed with saline, dried over magnesium sulfate, concentrated, and the resulting material chromatographed on silica gel eluting with methanol/dichloromethane (4/96). The appropriate fractions are pooled and concentrated to give 1-benzyl-1,2,3,6-tetrahydro-4-(4-methoxyphenyl)pyridine (XVI), MS (m/z) 279; IR (mineral oil) 1515, 738, 1030, 1258, 1250 and 1241 cm-1.

1. temperatureis heated at 76° for 3 min
2. temperatureThe resulting slurry is cooled
3. extractionThe mixture is extracted several times with dichloromethane
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated
6. customthe resulting material chromatographed on silica gel eluting with methanol/dichloromethane (4/96)
7. concentrationconcentrated