4-(Dimethylamino)cyclohexanone

light yellow oily liquid

Reference Example 8 REFERENCE EXAMPLE 174 The title compound from Step A above (20 g, 1 eq) in 6N con. HCI (150 ml.) was heated at reflux temperature for 2 h (-100 C). After the completion of the reaction, the reaction mixture was basified with potassium carbonate (pH = 14) and stirred well. The solid was filtered and the filtrate was extracted with dichloromethane (200 ml.) and the organic phase washed with brine. The organic phase was separated, dried over Na2S04 and the solvent removed under reduced pressure to afford the title compound as brown liquid (12 g, 79%). MS: 142.2 (M+H)+.4-dimethylamino-1-cyclohexanone 4.96 gm (26.8 mMol) 4-dimethylamino-l-cyclohexanone ethylene ketal were dissolved in 50 mL formic acid and the solution stirred at reflux for 18 hours. The reaction mixture was then cooled to ambient and the volatiles removed under reduced pressure to give 3.78 gm (100%) of the title compound.4-dimethylamino-1-cyclohexanone 4.96 gm (26.8 mMol) 4-dimethylamino-1-cyclohexanone ethylene ketal were dissolved in 50 mL formic acid and the solution stirred at reflux for 18 hours. The reaction mixture was then cooled to ambient and the volatiles removed under reduced pressure to give 3.78 gm (100%) of the title compound.4-Dimethylaminocyclohexanone 45.3 g of 8-dimethylamino-1, 4-dioxaspiro[4.5]decane (Compound 1 in Example XXXV) are stirred in 400 ml of 2N hydrochloric acid at room temperature for 3 days. The solution is then extracted three times with diethyl ether, and the aqueous phase is saturated with potassium carbonate and extracted five times with ethyl acetate. The combined organic phases are then dried over sodium sulphate, and the solvent is distilled off in a rotary evaporator. The residue is employed without further purification in the next reaction. Yield: 30.6 g (88% of theory) of pale brown oil, Rf: 0.53 (silica gel; methylene chloride/methanol/concentrated ammonia=10:2:0.1)To a stirred solution of the title compound from Step B above (10.0 g, 70.82 mmol) in ethanol, hydroxylamine hydrochloride (7.38 g, 106.23 mmol) and potassium carbonate (29.3 g, 212.46 mmol) were added and the reaction mixture was heated at 80C in an oil bath for 2 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product was diluted with ethyl acetate (150 ml.) and water (100 ml_). The organic phase was separated, dried over Na2S04, filtered and the solvents were removed under reduced pressure to get the crude compound as brown liquid which was directly taken to the next step without further purifications (8.8 g, 72%). MS: 157 (M+H)+. A solution of 18.4 gm (81 mMol) The preferred compounds of formula (3) are as follows: ... 14. 4-methylaminocyclohexanone 15. The preferred compounds of formula (3) are as follows: 1. cyclohexanone ... 11. 4-phenyloxycyclohexanone 12. 4-methyloxycyclohexanone 13. 4-nonyloxycyclohexanone 14. 4-methylaminocyclohexanone 15. A solution of 18.4 gm (81 mMol) Removal of ketal A solution of 18.4 gm (81 mMol) of Starting from A solution of 18.4 gm (81 mMol) a) 4-((dimethylamino)cyclohex-1-en-1-yl)trifluoromethane sulphonate

Molecular Weight:141.21
XLogP3:0.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:141.115364102
Monoisotopic Mass:141.115364102
Topological Polar Surface Area:20.3
Heavy Atom Count:10
Complexity:121
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes