Chlorotrimethylsilane → HCID 12595612, compound

8-Dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile (21 g, 0.1 mmol), dissolved in THF (210 ml), was added to a 1.82 M phenylmagnesium chloride solution in THF (109 ml, 0.198 mol) in the course of 15 min, under argon and while cooling with ice, and the mixture was then stirred at room temperature for 16 h. For working up of the reaction mixture, saturated ammonium chloride solution (150 ml) was added, while cooling with ice, and the mixture was extracted with diethyl ether (3×100 ml). The organic phase was extracted by shaking with water (100 ml) and saturated NaCl solution (100 ml) and the extract was concentrated. A yellow oil (25.2 g) remained. The crude product was dissolved in ethyl methyl ketone (280 ml), and ClSiMe3 (18.8 ml, 0.15 mol) was added, while cooling with ice. After a reaction time of 6 h, it was possible to isolate dimethyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine hydrochloride in a yield of 35% (10.5 g) as a white solid.

1. temperaturewhile cooling with ice
2. additionwas added
3. temperaturewhile cooling with ice
4. extractionthe mixture was extracted with diethyl ether (3×100 ml)
5. extractionThe organic phase was extracted
6. stirringby shaking with water (100 ml) and saturated NaCl solution (100 ml)
7. concentrationthe extract was concentrated
8. dissolutionThe crude product was dissolved in ethyl methyl ketone (280 ml)
9. temperaturewhile cooling with ice
10. customAfter a reaction time of 6 h, it

ORD record

ord-525024e589ec4727b3d83f32c3681a52

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138187B2