N-[4-(1H-Imidazol-1-yl)butyl]formamide → 4-(1H-Imidazol-1-yl)-N-methylbutan-1-amine

A solution of 58.8 g of N-[4-(1H-imidazol-1-yl)butyl]formamide in 480 ml of dry tetrahydrofuran was treated with 87.0 ml of 10 Molar borane methyl sulfide complex in tetrahydrofuran. The reaction mixture was heated to reflux for 18 hours under an argon atmosphere, cooled in an ice bath and quenched with 400 ml of methanol. The solvent was removed, the methanol addition and evaporation repeated, and the residue was made acidic with hydrochloric acid and was stirred over night. The mixture was made basic with sodium hydroxide solution and was extracted with dichloromethane. The combined organic layers were dried over potassium carbonate and evaporated to give an oil which was distilled to give 35.9 g (68%) of 4-(1H-imidazol-1-yl)-N-methylbutanamine, bp 130°-135° C./0.3 mm. The product was further characterized as the picrate, mp 111-113.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 18 hours under an argon atmosphere
3. temperaturecooled in an ice bath
4. customquenched with 400 ml of methanol
5. customThe solvent was removed
6. additionthe methanol addition and evaporation
7. extractionwas extracted with dichloromethane
8. dry with materialThe combined organic layers were dried over potassium carbonate
9. customevaporated
10. customto give an oil which
11. distillationwas distilled

ORD record

ord-4403d35c0e074fb4896d16a2efb5da5e

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04551460