Methyl iodide → HCID 22633405, compound

Participants

Reaction Steps

Potassium hydride oil suspension (3.80 g of 35%; 33 mmoles) was washed with hexane, 15 mL of tetrahydro-furan was added, and the suspension was treated with 4.25 g (16 mmoles) of 4-(3′-chlorophenyl)-α, 1-dimethyl-4-piperidinemethanol (Example 1) dissolved in 15 mL of tetrahydrofuran. The mixture was stirred at room temperature for 1 hour; methyl iodide (9.1 g, 64 mmoles) was added which caused the temperature to rise to 50° C. Methanol (5 mL) was added after stirring for 2.75 hours, keeping the temperature below 25° C. Water and chloroform were added, and the mixture was filtered to remove 4.70 g of the methiodide of the title compound. This solid was combined with the products obtained on removal of the solvent from the chloroform layer, and heated with 7.0 g of potassium methylmercaptide in 30 mL of dimethyl formamide in an 80° C. oil bath for 2.5 hours. The solvent was removed, water was added to the residue and the mixture was extracted with methylene chloride. Removal of the solvent from the dried extracts and short-path distillation of the residue (130° C. bath temperature, 1 micron) gave 3.94 g (88% yield) of the title compound as an oil. 1H NMR (CDCl3): δ 7.2-7.4 (m,4H); 3.3 (s,3H); 3.2 (quartet, J=7 Hz,1H); 2.7 (m,2H); 2.2 (s,3H); 1.8-2.4 (m,6H); and 0.9 (d,J=7 Hz,3H). High resolution mass spectrum: m/e calcd. for C15H22ClNO: 267.1390; measured: 267.1393.

Provenance & Evidence