Sodium Carbonate → Tert-butyl 4-(4-cyanophenyl)piperidine-1-carboxylate

To a solution of tert-butyl 4-[4-(aminocarbonyl)phenyl]-1-piperidinecarboxylate (3.34 g) in DMF (18 ml) was dropwise added phosphoryloxychloride (3.07 ml) keeping under 10° C. with stirring and the mixture was stirred at ambient temperature for 10 minutes. The reaction mixture was poured into a mixture of saturated aqueous sodium carbonate (60 ml) and ice-water (250 ml) with stirring and extracted twice with a mixture of ethyl acetate (200 ml) and hexane (80 ml). The extract was washed twice with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (300 ml) eluting with a mixture of n-hexane and ethyl acetate (4:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give tert-butyl 4-(4-cyanophenyl)-1-piperidine carboxylate (3.13 g).

1. customkeeping under 10° C.
2. stirringthe mixture was stirred at ambient temperature for 10 minutes
3. stirringwith stirring
4. extractionextracted twice with a mixture of ethyl acetate (200 ml) and hexane (80 ml)
5. washThe extract was washed twice with saturated aqueous sodium chloride
6. dry with materialdried over magnesium sulfate
7. customevaporated in vacuo
8. customThe resulting residue was chromatographed on silica gel (300 ml)
9. washeluting with a mixture of n-hexane and ethyl acetate (4:1 v/v)
10. additionThe fractions containing the desired compound
11. customwere collected
12. customevaporated under reduced pressure

ORD record

ord-50dcbdd26431424fb9703970ffb4b897

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884774B2