Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.COC(=O)[C:17]([CH2:19][Cl:20])=O.[OH-].[NH4+]>CO.[Cl-].[Na+].O>[Cl:20][CH2:19][CH:17]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1A suspension of 108.4 g (0.55 mol) of tryptaminehydrochloride in 1 liter of dry methanol and 93.2 g (0.68 mol) of methyl-3-chloropyruvate* was refluxed under N2 for 24 h. The cooled mixture was poured into brine, made basic with ammonium hydroxide and extracted with dichloromethane. Concentration and trituration with ethyl acetate gave 94.0 g (61.3%) of the chloromethyl tetrahydro-β-carboline, melting point ("mp") 123°-125° C. The product was recrystallized from dichloromethane/pentane.
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