Dimethyl Sulfoxide → HCID 13876719, compound

To a solution of oxalyl chloride (5.8 ml) in dichloromethane (100 ml) were added dropwise dimethyl sulfoxide (9.44 ml), a solution of 1-benzyl-4-(1-hydroxyethyl)-1,2,3,6-tetrahydropyridine (13.7 g) in dichloromethane (30 ml) and triethylamine (44.2 ml ) under nitrogen atmosphere at -70° C. Then, the reaction mixture was allowed to warm at ambient temperature and precipitate was filtered off. The filtrate was concentrated in vacuo and the residue was dissolved in a mixture of ethyl acetate (200 ml) and water (100 ml). The organic layer was separated, washed with brine (100 ml), dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (350 ml) eluting with a mixture of hexane and ethyl acetate (1:1, V/V) to give 4-acetyl-1-benzyl-1,2,3,6-tetrahydropyridine (9.63 g).

1. customat -70° C
2. filtrationprecipitate was filtered off
3. concentrationThe filtrate was concentrated in vacuo
4. dissolutionthe residue was dissolved in a mixture of ethyl acetate (200 ml) and water (100 ml)
5. customThe organic layer was separated
6. washwashed with brine (100 ml)
7. dry with materialdried over magnesium sulfate
8. customEvaporation of the solvent
9. customgave a residue, which
10. customwas chromatographed on silica gel (350 ml)
11. washeluting with a mixture of hexane and ethyl acetate (1:1, V/V)

ORD record

ord-3ad6294d05064cd0b85e994a37095726

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05102877