Hydrochloric Acid → 4-(Dimethylamino)cyclohexan-1-one

To a suspension of 1,4-cyclohexanedione monoethyleneketal (3.82 g, 24.6 mmol) and dimethylamine hydrochloride (2.00 g, 24.6 mmol) in 1,2-dichloroethane (50 ml) were dropwise added triethylamine (4.2 ml, 29.6 mmol) and DBU (1,8-diazabicyclo-[5.4.0]-7-undecene) (4.4 ml), and the mixture was stirred for 10 minutes. To the mixture was added triacetoxyborohydride (7.68 g, 34.4 mmol), and the mixture was stirred for 4.5 hours. Precipitate was filtered off, and the filtrate was concentrated to give crude product (6.34 g), which was dissolved in water (10 ml). To the mixture was dropwise added concentrated hydro-chloric acid (6 ml), and the mixture was stirred for 48 hours. The reaction mixture was diluted with water and washed twice with ether. The aqueous layer was made basic with sodium hydroxide and extracted with ether twice. The extract was washed with saturated sodium chloride solution, dried with potassium carbonate and purified by evaporation to give 4-dimethylaminocyclohexanone (0.59 g, 17%).

1. stirringthe mixture was stirred for 4.5 hours
2. filtrationPrecipitate was filtered off
3. concentrationthe filtrate was concentrated
4. customto give crude product (6.34 g), which
5. stirringthe mixture was stirred for 48 hours
6. washwashed twice with ether
7. extractionextracted with ether twice
8. washThe extract was washed with saturated sodium chloride solution
9. dry with materialdried with potassium carbonate
10. custompurified by evaporation

ORD record

ord-08aa566d133f4172be146a1399fea011

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06166006