Hydrochloric Acid → (RS)-1-(7-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-propylamine hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of lithium aluminium hydride (1.0 M in THF, 2.7 mL, 2.7 mmol) in added THF (5 mL) under argon was added dropwise a solution of 1-(7-chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-nitro-1-propene (0.5 g, 1.8 mmol) in THF (10 mL). The mixture was heated under reflux for 4 h and cooled to 0° C. To the mixture was added dropwise aqueous potassium sodium tartrate solution (50 mL) and the mixture was stirred for 30 min and filtered through kieselguhr. The filtrate was extracted with dichloromethane (3×30 mL). The combined organic extracts were washed (water, brine), dried (sodium sulfate), concentrated in vacuo, treated with ethereal hydrogen chloride (1.0 M, 2 mL, 2 mmol) and concentrated in vacuo. The concentrate was recrystallised (2-propanol) to give the title compound as a white solid (0.23 g, 45%): mp 272-273° C.; Found: C, 57.86; H, 6.37; N, 9.41%. C14H17ClN2.HCl. 0.25H2O requires: C, 58.03; H, 6.39; N, 9.67%.

Provenance & Evidence