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

HRID 1637871Notes

Reaction equation

HRID 1637871 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][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.C(O)(C(F)(F)F)=O>>[CH3:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]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:16][CH:15]=1

Participants

4

Reactant 3

HCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 77254-Methylbenzaldehyde

Product 1

HCID 33525052,3,4,9-Tetrahydro-1-(4-methylphenyl)-1H-pyrido[3,4-b]indoleYield 100%

Procedure

This product was prepared using the same procedure as for Intermediate 1 with tryptamine (1.0 g, 6.2 mmol), 4-methylbenzaldehyde (0.74 g, 1 equiv.) and TFA (1 mL, 2 equiv.) to give the title compound (1.6 g, 100%) as a white powder. MP: 207-209° C.

Workup

  1. customThis product was prepared

Sources & evidence

ORD record
ord-fef35e02808b45f1bfd9ec448876e2e8
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

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