[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[CH3:14].N1(C(N2CCCCC2)N2CCCCC2)CCCC[CH2:20]1.O>C(Cl)Cl.[Fe].C1(C)C=CC=CC=1.C(O)(=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:6]=1[CH:14]=[CH:20][NH:11]2
A mixture of 16 g (0.06 mol) of 2-(2-chlorobenzyl)-6-nitrotoluene and 24.4 g (0.09 mol) of tripiperidinomethane is heated for 5 hours at 120° C. in a water jet vacuum with interconnection of a distillation assembly. Then the mixture is taken up in 200 ml of a mixture of 5 parts of toluene and 3 parts of glacial acetic acid and under stirring is added to a suspension of 144 g of iron powder and 362 g of silica gel in 800 ml the same toluene-glacial acetic acid mixture. The reaction mixture is refluxed for 1 hour under an argon atmosphere. After cooling it is diluted with methylene chloride and filtered off from a precipitate. The filtrate in succession is washed with 10% sodium carbonate solution, 5% sodium bisulfite solution and saturated common salt solution and then dried on sodium sulfate. The solution is concentrated by evaporation, the residue after chromatography on silica gel with a mixture of 4 parts of cyclohexane and one part of ethyl acetate and recrystallization from cyclohexane yields 9 g (58% of theory) of 4-(2-chlorobenzyl)-indole, melting point 76°-77° C.
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