Hydrochloric Acid → 1-Acetyl-4-(4-aminophenyloxy) piperidine

1-Acetyl-4-(4-nitrophenyloxy) piperidine (4.72 g) was dissolved in ethanol (50 ml) and to the mixture was added conc. hydrochloric acid (2.5 ml). By using 10% palladium/carbon as a catalyst, catalytic reduction was conducted at a normal temperature and normal pressure. After completion of the reaction, the catalyst was removed and the solvent was distilled off. To the residual oily compound was added water (20 ml). The solution was made basic with addition of solid potassium carbonate and extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain an oily compound of 1-acetyl-4-(4-aminophenyloxy) piperidine (3.9 g). The oily compound (1.77 g) was dissolved in dimethylformamide (10 ml) and to the mixture were added potassium carbonate (2.1 g) and 1,4-dibromobutane (0.9 ml), followed by heating with stirring at 100° C. for one hour. After completion of the reaction, water (50 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then the solvent was distilled off. The residual oily compound was separated and purified by silica gel column chromatography and then recrystallized from ethyl acetate/ethyl ether to obtain colorless crystals (1.5 g), m.p. 69°-70° C.

1. customAfter completion of the reaction
2. customthe catalyst was removed
3. distillationthe solvent was distilled off
4. additionTo the residual oily compound was added water (20 ml)
5. additionThe solution was made basic with addition of solid potassium carbonate
6. extractionextracted with ethyl acetate
7. dry with materialAfter drying over anhydrous magnesium sulfate
8. distillationthe solvent was distilled off

ORD record

ord-621d8ec6a09c4965b45dbccb81cf6a33

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05580883