1,2,3,4-Tetrahydroisoquinoline → HCID 21830900, compound

Participants

Reaction Steps

A solution of ethyl bromoacetate (20.9 g) in acetonitrile (30 mL) was added to a mixture of K2CO3 (27.6 g, 0.2 mol) and 1,2,3,4-tetrahydro-2-isoquinoline (13.3 g, 0.1 mol) in acetonitrile (220 mL). The reaction mixture was stirred at room temperature for about 2 days, and then was refluxed for 4 hours. The reaction mixture was filtered, the filtrate was concentrated in vacuo and the residue was partitoned between ether and water. The ether layer was separated, dried over MgSO4 and concentrated in vacuo to afford a liquid which was dissolved in ether (200 mL), cooled and treated with Et2O·HCl to afford 12,5 g (77%) of ethyl 1,2,3,4-tetrahydro-2-isoquinolinylacetate hydrochloride.

Provenance & Evidence