Water → 4-(N-cyclohexyl-N-methylaminomethyl)aniline

To a solution of N-cyclohexyl-N-methyl-N-(4-nitrobenzyl)amine (12.4 g, 50.0 mmol) in methanol(250 ml) were added nickel bromide (1.09 g, 5.0 mmol) and then sodium boron hydride (7.57 g, 200 mmol) at 0° C., and the mixture was stirred at room temperature for 30 minutes. To the mixture were added nickel bromide (0.55 g, 2.5 mmol) and then sodium boron hydride (3.78 g, 100 mmol) at 0° C., and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added water (100 ml), and the mixture was concentrated under reduced pressure. To the residue was added ethyl acetate, and insoluble material was filtered off with Celite. The filtrate was washed with ethyl acetate, and the ethyl acetate layer was dried with MgSO4 and concentrated under reduced pressure. The residue was washed with hexane to give 4-(N-cyclohexyl-N-methylaminomethyl)aniline (3.99 g, 37%).

1. concentrationthe mixture was concentrated under reduced pressure
2. additionTo the residue was added ethyl acetate, and insoluble material
3. filtrationwas filtered off with Celite
4. washThe filtrate was washed with ethyl acetate
5. dry with materialthe ethyl acetate layer was dried with MgSO4
6. concentrationconcentrated under reduced pressure
7. washThe residue was washed with hexane

ORD record

ord-8185f1979137423a929adb6445430b62

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376536B1