C(O[CH:4](OCC)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)C.Cl.[OH:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[OH:28])[CH2:22][CH2:23][NH2:24].C(O)CCC>O>[ClH:13].[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([NH:6][CH2:5][CH:4]2[C:25]3[C:21](=[CH:20][C:19]([OH:18])=[C:27]([OH:28])[CH:26]=3)[CH2:22][CH2:23][NH:24]2)=[CH:12][CH:11]=1p-Chloroanilinoacetaldehyde diethyl acetal (486 mg) and 3,4-dihydroxyphenethylamine hydrochloride (378 mg) were added to a mixture of n-butyl alcohol (4 ml) and water (0.4 ml) and then the mixture was refluxed for 3.5 hours. The above-mentioned acetal (0.24 g) was further added thereto and the resultant mixture was refluxed for 3 hours. The reaction mixture was treated in a conventional manner to give 1-(p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride. This product was identified by thin-layer chromatography on silica gel [Developing solvent: (n-butyl alcohol:acetic acid:water=8:1:1)] with an authentic sample, mp 91° to 93° C., which was obtained by reacting 1-(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride obtained in Example 1(D) with conc. hydrochloric acid and acetic acid.
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