Tetrahydrofuran → N-(4'-chloro-2'-fluoro-5'-isopropyloxyphenyl)-4-(trifluoromethyl)-2-piperidone

Temperature

50 °C

To a tetrahydrofuran (16 ml) solution of 1.4 g (3.6 mmol) of N-(4'-chloro-2'-fluoro-5'-isopropyloxyphenyl)-5-chloro-3-(trifluoromethyl)pentanamide were added 16 ml water and 2 ml 50% NaOH (aq). The mixture was heated to 50° C. while stirring vigorously. After 6 hours the reaction was allowed to cool to room temperature, stirring was stopped and the aqueous layer was removed. The organic layer was evaporated in vacuo, then the residue was taken up in ether (50 ml), washed with water (2×50 ml) and then brine. The original aqueous layer was extracted with a second 50 ml portion of ether, the combined organic layers were washed with brine (50 ml) and dried (MgSO4). The solvent was removed in vacuo to yield 1.3 g. of a brown solid which was recrystallized from hexanes to yield 0.81 g (64% yield) of a brown solid (m.p. 98°-102° C.).

1. temperatureto cool to room temperature
2. stirringstirring
3. customthe aqueous layer was removed
4. customThe organic layer was evaporated in vacuo
5. washwashed with water (2×50 ml)
6. extractionThe original aqueous layer was extracted with a second 50 ml portion of ether
7. washthe combined organic layers were washed with brine (50 ml)
8. dry with materialdried (MgSO4)
9. customThe solvent was removed in vacuo
10. customto yield 1.3 g
11. customof a brown solid which was recrystallized from hexanes

ORD record

ord-4a264690a3cf4366a1cea2c8334b866e

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05502027