Iodine → 2-(1-Benzyl-4-heptyl-4-piperidyloxy)-ethanol

Participants

Reaction Steps

A solution of 101.5 g of n-heptyl bromide in 300 ml was added over 1 hour under a nitrogen atmosphere to a flask containing 9.6 g of magnesium turnings, 50 ml of ether, 3 drops of ethyl iodide and an iodine crystal and the mixture was stirred for 1 hour. A solution of 46.6. g of 8-benzyl-1,4-dioxa-8-azaspiro [4,5] decane in 1 liter of anhydrous benzene was added to the resulting solution and after removal of the ether, the mixture was refluxed for 16 hours. The solution was then cooled and 20 ml of water followed by 400 ml of a saturated aqueous ammonium chloride solution was added with stirring. The organic phase was decanted and the solvent was distilled under reduced pressure. The residue was rectified to obtain 40 g of 2-(1-benzyl-4-heptyl-4-piperidyloxy)-ethanol as an oil distilling between 150° to 200° C. The oil was used as is for the next step.

Provenance & Evidence