Tryptamine → 1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][CH2:21][NH2:22])=[CH:12]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[C:12]3[NH:11][C:19]4[C:14]([C:13]=3[CH2:20][CH2:21][NH:22]2)=[CH:15][CH:16]=[CH:17][CH:18]=4)=[CH:5][CH:4]=1

Participants

Procedure

To a 0.5 M solution of 4-methoxybenzaldehyde in dichloromethane (800 μl) was added a 0.25 M solution of 2-(1H-indol-3-yl)ethanamine in dichloromethane (800 μl) followed by trifluoracetic acid (20 μl). The mixture was sealed and shaken at room temperature for 24 hours. The mixture was evaporated to dryness resuspended in toluene (1 ml) vortexed and re-evaporated to dryness. To the residue was added methanol (1.5 ml) and dichloromethane (1 ml). After vortexing the solution was filtered through a pre-washed (methanol, 5 ml) SCX cartridge (Bakerbond JT7090-07, aromatic sulfonic acid). 1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole, was eluted from the cartridge with 0.5 M aqueous ammonia in methanol (5 ml). Evaporation to dryness gave 1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole that was used directly for the next step.