Hydrochloric Acid → N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-1-methylisoquinoline hydrochloride

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Reaction Steps

N-(4-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7- dimethoxy-1-methylisoquinoline (62.9 g, 0.17 m) was added portionwise to 500 ml of 1 M borane in THF which was diluted with 500 ml THF and maintained under nitrogen. The mixture was stirred at ambient temperature for 1 hr, then heated to reflux for 4 hr. The mixture was then cooled in an ice bath and treated carefully with 20% HCl (250 ml). The mixture was refluxed for 1 hr, cooled and then the solvents evaporated on an aspirator. Water (1 liter) was added and the solution basified to pH 11 with 50% NaOH, then extracted with CHCl3 (3×300 ml). The extracts were dried over MgSO4 and evaporated to an oily residue. The residue was dissolved in 300 ml of 1:1 methanol:isopropanol and treated with HCl gas until acidic. Upon cooling, a yellow solid was obtained which was collected by filtration and air dried to give 66.4 g (100+%) N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-1-methylisoquinoline hydrochloride. The product was slightly wet with isopropanol.

Provenance & Evidence