Ammonium Chloride → HCID 12595611, compound

30 g 8-dimethylamino-1,4-dioxaspiro[4.5] decane-8-carbonitrile were dissolved in 300 ml tetrahydrofuran, 143 ml 2.0 molar phenyl magnesium chloride solution in THF were added under a nitrogen atmosphere and stirred overnight at ambient temperature. To work up the mixture, 100 ml ammonium chloride solution (20% by weight) were added with ice cooling, the phases were separated, the aqueous phase was extracted twice with 250 ml diethylether in each case, the combined organic phases were dried over sodium sulfate, filtered, concentrated and substantially freed from solvent residues under vacuum. The crude dimethyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine (34.5 g) obtained was stirred for 48 hours with a mixture of 83 ml concentrated hydrochloric acid (32% by weight) and 48 ml water at ambient temperature without further purification. Subsequently the reaction mixture was first washed three times with 50 ml diethylether in each case, then alkalized by addition of 100 ml sodium hydroxide solution (32% by weight) with ice cooling, extracted three times with 100 ml dichloromethane in each case, the combined dichloromethane extracts were dried over sodium sulfate, filtered, concentrated and substantially freed of solvent residues under vacuum. 18.8 g 4-dimethylamino-4-phenylcyclohexanone were obtained.

1. additionwere added with ice cooling
2. customthe phases were separated
3. extractionthe aqueous phase was extracted twice with 250 ml diethylether in each case
4. dry with materialthe combined organic phases were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-b972a3116f0a46168801646a5e786226

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183436B2