Water → HCID 70057865, compound

Participants

Reaction Steps

To a suspension of (±)-3-hydroxy-1-pentylquinuclidinium bromide (20 g, 72 mmol) in dry 1,2-dimethoxyethane (150 ml) at 0° C., under nitrogen, was added sodium hydride (3.48 g, 60% in mineral oil, 86.8 mmol) and then iodomethane (11.3 ml, 181 mmol). The temperature was allowed to rise to room temperature overnight. Water (200 ml) was added and the mixture was extracted with 6×100 ml dichloromethane. Drying and evaporation gave an oily residue which, after trituration with petrol ether, gave the title compound as a crystalline solid. Yield 23.9 g (That the yield was more than 100% is explained by the fact that there is a mixture of bromide and iodide as counter ions.).

Provenance & Evidence