Water → 2-(1-(4-Fluorobenzyl)piperidin-4-yl)ethan-1-ol

A mixture of 4-(2-hydroxyethyl)piperidine (21.5 g), 4-fluorobenzaldehyde (17.5 ml) and p-toluene sulfonic acid (3 mg) in benzene (200 ml) was refluxed with separating water as the benzene azeotrope. After 2 hours, the mixture was evaporated in vacuo. The residue was dissolved in methanol (200 ml) and sodium borohydride (6.3 g) was added thereto at 5° C. After stirring at ambient temperature for 1 hour, the mixture was evaporated in vacuo. 4N Hydrochloric acid (200 ml) was added to the residue and washed with ethyl acetate. The aqueous layer was made basic to pH 10 with potassium carbonate and extracted with ethyl acetate. The extract was washed with water and brine, and dried over magnesium sulfate, and evaporated in vacuo to give 1-(4-fluorobenzyl)-4-(2-hydroxyethyl)piperidine (32.0 g) as an oil.

1. customthe mixture was evaporated in vacuo
2. dissolutionThe residue was dissolved in methanol (200 ml)
3. additionsodium borohydride (6.3 g) was added
4. customat 5° C
5. customthe mixture was evaporated in vacuo
6. addition4N Hydrochloric acid (200 ml) was added to the residue
7. washwashed with ethyl acetate
8. extractionextracted with ethyl acetate
9. washThe extract was washed with water and brine
10. dry with materialdried over magnesium sulfate
11. customevaporated in vacuo

ORDレコード

ord-81c94a8cf3a54d16a3ac4f055b91e857

出典データセット

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05622976