Hydrochloric Acid → HCID 57475098, compound

(8-butyl-1,4-dioxa-spiro[4.5]dec-8-yl)-dimethylamine hydrochloride (41.8 g, 0.15 mmole) was dissolved in water (78 ml) and 37% hydrochloric acid (100 ml, 1.2 mole) was added while stirring and cooling with ice. The clear reaction mixture was stirred for 7 days at room temperature. After completion of the hydrolysis the reaction mixture was extracted with diethyl ether (2×70 ml). The organic extracts were discarded. The aqueous phase was made alkaline with 5N sodium hydroxide solution (approximately 250 ml) while cooling with ice, and vigorously stirred. The solution was extracted with diethyl ether (3×100 ml). The combined organic extracts were washed with water (2×70 ml), dried and concentrated by evaporation. 4-butyl-4-dimethylamino-cyclohexanone (Ket-9) was obtained as a pale brown oil in a yield of 96% (28.4 g). The yield of ketone—referred to the ketal used in the first stage—was 75%.

1. temperaturecooling with ice
2. stirringThe clear reaction mixture was stirred for 7 days at room temperature
3. customAfter completion of the hydrolysis the reaction mixture
4. extractionwas extracted with diethyl ether (2×70 ml)
5. temperaturewhile cooling with ice
6. stirringvigorously stirred
7. extractionThe solution was extracted with diethyl ether (3×100 ml)
8. washThe combined organic extracts were washed with water (2×70 ml)
9. customdried
10. concentrationconcentrated by evaporation

ORD record

ord-a0d7a0d1d23e4ccfa6198c2c25231338

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399503B2