Hexane → HCID 18542656, compound

Temperature

40 °C

A solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-chloro-5-methoxycarbonylnitrobenzene (3.4 g) in concentrated hydrochloric acid (30 ml) was stirred at 75° C. for 16 hours. The reaction mixture was concentrated in vacuo. To a solution of the residual colorless solid in a mixture of water (15 ml) and acetone (15 ml) were added sodium hydrogencarbonate (1.6 g) and di-t-butyldicarbonate (2.2 g) in an ice bath. The resulting mixture was stirred at 40° C. for 1 hour. The reaction mixture was extracted with ethyl acetate. The extract was washed with 0.5M hydrochloric acid, water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo to afford a pale yellow solid. To the solid was added hexane and the mixture was filtered to give the desired compound (2.6 g, yield 79%) as a pale yellow solid.

1. concentrationThe reaction mixture was concentrated in vacuo
2. additionTo a solution of the residual colorless solid in a mixture of water (15 ml) and acetone (15 ml)
3. additionwere added sodium hydrogencarbonate (1.6 g) and di-t-butyldicarbonate (2.2 g) in an ice bath
4. extractionThe reaction mixture was extracted with ethyl acetate
5. washThe extract was washed with 0.5M hydrochloric acid, water and brine
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationthe filtrate concentrated in vacuo
9. customto afford a pale yellow solid
10. filtrationthe mixture was filtered

ORD record

ord-3030018ad4774dceb87336de9964a3e0

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555556B1