Furfurylamine → 4-(Furan-2-yl)butan-1-amine

A solution of furfurylamine (1.0 g) in dry DMF (3 ml) was added to a cooled (0°-5° C.) stirred suspension of sodium hydride (60% dispersion; 0.46 g) in DMF (5 ml). After 15 minutes, a solution of 1-bromopropane (1.3 g) in dry DMF (2 ml) was added over 5 minutes. Stirring was continued for 1 h and the reaction mixture was then allowed to warm to room temperature and stirred overnight. The reaction was quenched by the addition of dilute hydrochloric acid. Aqueous sodium hydrogen carbonate solution (100 ml) was then added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with water, brine and then dried (magnesium sulphate) and evaporated in vacuo. The residue was distilled under reduced pressure to furnish the title compound (0.21 g) as a colourless liquid.

1. temperaturea cooled (0°-5° C.)
2. stirringStirring
3. waitwas continued for 1 h
4. stirringstirred overnight
5. customThe reaction was quenched by the addition of dilute hydrochloric acid
6. additionAqueous sodium hydrogen carbonate solution (100 ml) was then added
7. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
8. washThe combined organic extracts were washed with water, brine
9. dry with materialdried (magnesium sulphate)
10. customevaporated in vacuo
11. distillationThe residue was distilled under reduced pressure

ORD record

ord-de542e665cf24b499fea501fcace5c3f

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05773467