Allylamine → HCID 19600057, compound

To a solution of the crude 2-(3-hydroxymethylfuran-2-yl)ethanol and 1.74 ml (9.96 mmol) of N,N-diisopropylethylamine in 50 ml of dichloromethane, 0.71 ml (9.13 mmol) of methanesulfonyl chloride was added dropwise under ice-cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with water and then saturated sodium chloride. After which it was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 50 ml of ethanol, 0.36 g (6.22 mmol) of allylamine and 2.38 ml (13.7 mmol) of N,N-diisopropylethylamine were added, followed by overnight stirring at 80° C. The solvent was distilled off under reduced pressure from the reaction mixture; the resulting crude product was purified by silica gel column chromatog-raphy (hexane/ethyl acetate=9/1 to 6/1) to yield 5-allyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine.

1. temperaturecooling
2. washwashed with water
3. dry with materialAfter which it was dried over anhydrous magnesium sulfate
4. distillationthe solvent was distilled off under reduced pressure
5. dissolutionThe resulting residue was dissolved in 50 ml of ethanol
6. waitfollowed by overnight
7. stirringstirring at 80° C
8. distillationThe solvent was distilled off under reduced pressure from the reaction mixture
9. customthe resulting crude product was purified by silica gel column chromatog-raphy (hexane/ethyl acetate=9/1 to 6/1)

ORD record

ord-5412f4297ac149cc89ac197d02a680c9

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998433