Chlorotrimethylsilane → HCID 57475095, compound

2 M benzylmagnesium chloride solution in THF (3, 285 ml, 570 mmol) was added to a solution of 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (39.8 g, 190 mmol) in THF (300 ml) in the course of 15 min, under argon and while cooling with ice. The mixture was then stirred at RT for 16 h. For working up of the reaction mixture, saturated ammonium chloride solution (200 ml) and water (100 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 (50 ml) and saturated NaCl solution (50 ml) and the extract was then concentrated. A white solid (68.34 g) remained which, apart from the product, still contained the educt. The crude product was dissolved in ethyl methyl ketone (250 ml), and ClSiMe3 (30 ml, 238 mmol) was added, while cooling with ice. After 16 h, dimethyl-(8-benzyl-1,4-dioxa-spiro[4.5]dec-8-yl)amine hydrochloride was isolated in a yield of 52% (40.33 g) as a white solid with a melting point of 276-280° C.

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 (50 ml) and saturated NaCl solution (50 ml)
7. concentrationthe extract was then concentrated
8. dissolutionThe crude product was dissolved in ethyl methyl ketone (250 ml)
9. temperaturewhile cooling with ice
10. waitAfter 16 h

ORD record

ord-eeab108a6ff0452d9337fdfb7b13e0b4

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138187B2