Formaldehyde → N-methyl-N-(3,5-dimethylcyclohexyl)-N-(4-nitrobenzyl)amine

In 1,2-dichloroethane (70 ml) were suspended p-nitrobenzylamine hydrochloride (3.8 g), 3,5-dimethylcyclohexanone (2.5 g) and triethylamine (2.8 ml). Under ice-cooling, to the mixture was added sodium triacetoxy boron hydride (5.9 g). Under nitrogen atmosphere, the mixture was stirred at room temperature over night. Under ice-cooling, to the mixture were added 37% formalin (1.8 ml) and sodium triacetoxy boron hydride (5.9 g). Under nitrogen atmosphere, the mixture was stirred at room temperature over night. The solvent was evaporated, and the residue was neutralized with sodium hydroxide. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give 3 isomers of N-methyl-N-(3,5-dimethylcyclohexyl)-N-(4-nitrobenzyl)-amine (4.3 g; (31-a), 0.7 g; (31-b), 0.2 g; (31-c)) as each yellow oil.

1. temperatureUnder ice-cooling, to the mixture
2. temperatureUnder ice-cooling, to the mixture
3. stirringUnder nitrogen atmosphere, the mixture was stirred at room temperature over night
4. customThe solvent was evaporated
5. extractionThe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with water and saturated sodium chloride solution
7. dry with materialdried with anhydrous magnesium sulfate
8. customUnder reduced pressure, the solvent was evaporated
9. customthe residue was purified with silica gel column (ethyl acetate/hexane)

ORDレコード

ord-0fb778d81b3a4c3bb52e855f8dad5de3

出典データセット

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06172061B2