[ClH:1].[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)C>C(#N)C.CCOCC>[ClH:1].[CH2:21]([N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[CH2:12]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline monohydrochloride (2.50 g, 11.6mmol) and potassium carbonate (2.0 g) in acetonitrile (100 ml) was added benzyl bromide (2.22 g, 13.0 mmol) in acetonitrile (10 ml). The solution was stirred overnight and the solid was then removed by filtration. The solvent was removed in vacuo to give a solid which was partitioned between methylene chloride and water. The dried (MgSO4) organic phase was concentrated and the resulting oil was taken up in ethanol (50 ml). This solution was made acidic with hydrochloric acid in ethanol. The precipitate which formed had set up solid and an additional 150 ml of ethanol and 50 ml of ether was added. The solid was collected and air dried to give 2-benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride as an off white solid (2.78 g (79%)), m.p. 256-8° C. (dec).
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