Chlorotrimethylsilane → HCID 12595612, compound

Participants

Reaction Steps

8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (21 g, 0.1 mole), dissolved in THF (210 ml), was added within 15 minutes while cooling with ice and under argon to a 1.82 M phenylmagnesium chloride solution in THF (109 ml, 0.198 mole) and the mixture was then stirred for 16 hours at room temperature. To work up the reaction mixture saturated ammonium chloride solution (150 ml) was added while cooling with ice and 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 concentrated by evaporation. 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 mole) was added while cooling with ice. After a reaction time of 6 hours dimethyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine hydrochloride was isolated as a white solid in a yield of 35% (10.5 g).

Provenance & Evidence