Sodium hydride → 4-(3-Piperidinomethylphenoxy)butaneamine

A mixture of 3-(1-piperidinylmethyl)phenol (8.7 g) and sodium hydride (1.2 g) in dimethylformamide (60 ml) was stirred at 25° during 3 h. N-(4-Bromobutyl)phthalimide (12.8 g) was added and the mixture was stirred at 25° during 20 h then at 65° for 3 h. The reaction mixture was poured onto water and extracted with ethyl acetate. The solvent was concentrated and the crystalline impurity was removed by filtration. The filtrate was evaporated in vacuo and the residue was dissolved in ethanol and heated at reflux with hydrazine hydrate (2.5 ml) for 3 h. The mixture was filtered and the filtrate distilled to give the title compound as a colourless oil (4.1 g) b.p. 140°/0.1 mm TLC silica, ethyl acetate/water/isopropanol/0.88 ammonia 25:8:15:2, Rf 0.32.

1. stirringthe mixture was stirred at 25° during 20 h
2. waitat 65° for 3 h
3. additionThe reaction mixture was poured onto water
4. extractionextracted with ethyl acetate
5. concentrationThe solvent was concentrated
6. customthe crystalline impurity was removed by filtration
7. customThe filtrate was evaporated in vacuo
8. dissolutionthe residue was dissolved in ethanol
9. temperatureheated
10. temperatureat reflux with hydrazine hydrate (2.5 ml) for 3 h
11. filtrationThe mixture was filtered
12. distillationthe filtrate distilled

ORDレコード

ord-8aa3e8f3658346bd9174949d6e98a5b9

出典データセット

uspto-grants-1988_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04764612