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

HRID 1637867Notes

Reaction equation

HRID 1637867 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C(O)(C(F)(F)F)=O>>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]2[C:5]3[NH:6][C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:4]=3[CH2:3][CH2:2][NH:1]2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 312444-Methoxybenzaldehyde

Product 1

HCID 1989161-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoleYield 80%

Procedure

This product was prepared using the same procedure as for Intermediate 1 with tryptamine (15 g, 94.9 mmol), 4-methoxybenzaldehyde (12.9 g, 1.1 equiv.) and TFA (14.6 mL, 2 equiv.) to give the title compound (20.9 g, 80%) as a brownish powder. MP: 131° C.

Workup

  1. customThis product was prepared

Sources & evidence

ORD record
ord-9a9a061b785a4bebb8375d40c50b94c3
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

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