Tryptamine → 1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 381471

Reaction equation

HRID 381471 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.[CH2:13]1[O:23][C:22]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=2[O:14]1.C(O)(C(F)(F)F)=O>>[CH2:13]1[O:23][C:22]2[CH:21]=[CH:20][C:17]([CH:18]3[C:5]4[NH:6][C:7]5[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=5)[C:4]=4[CH2:3][CH2:2][NH:1]3)=[CH:16][C:15]=2[O:14]1

Participants

4

Reactant 3

HCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 8438Piperonal

Product 1

HCID 2011721-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carbolineYield 62.7%

Procedure

This product was prepared using the same procedure as for Intermediate 1 with tryptamine (20.0 g, 120 mmol), 3,4-methylenedioxybenzaldehyde (20.6 g, 1.1 equiv.) and TFA (18 mL, 2 equiv.) to give the title compound (22 g, 60%) as white crystals after recrystallization from ethanol.

Workup

  1. customThis product was prepared

Sources & evidence

ORD record
ord-bdbfef5ddda649c9a23eb52eb002f8cb
Source dataset
uspto-grants-2001_10
Patent number
US06306870B1

Linked notes

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