Hydrochloric Acid → HCID 18448550, compound

Participants

Reaction Steps

HCl (1.2 mL, 37%) was added to a MeOH (60 mL) solution of 1-[4-(tert-butyl-dimethyl-silanyloxy)-chroman-8-ylmethyl]-piperidine (3.00 g, 8.30 mmol). After stirring for 1 h, the mixture was evaporated to dryness from benzene. The resulting crude alcohol was dissolved in SOCl2 (5 mL) and stirred for 3 days at RT. Following the removal of the excess SOCl2 in vacuo from hexane, the crude chloride was dissolved in DMF (20 mL) and NaN3 (1.618 g, 24.9 mmol) was added. The mixture was stirred at 80° C. for 1 h and, upon cooling, it was diluted with Et2O (100 mL), hexane (100 mL) and H2O (100 mL). After separation, the organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound. MS (APCI+, m/z): 273 (M+1)+.

Provenance & Evidence