Tryptamine → 1-Indan-5-yl-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 1637874Notes

Reaction equation

HRID 1637874 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[C:21]2[C:16](=[CH:17][C:18]([CH:22]=O)=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(O)(C(F)(F)F)=O>>[CH2:13]1[C:21]2[C:16](=[CH:17][C:18]([CH:22]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:19][CH:20]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 1216245-Indanecarboxaldehyde

Product 1

HCID 108807391-Indan-5-yl-2,3,4,9-tetrahydro-1H-beta-carbolineYield 15.6%

Procedure

This product was prepared using the same procedure as for Intermediate 1 with tryptamine (1.28 g, 8.0 mmol), indan-5-carboxaldehyde (1.3 g, 1.1 equiv.) and TFA (1.2 mL, 2 equiv.) to give the title compound (0.36 g, 14%). 1H NMR (CDCl3) δ 7.6 (s, 1H), 7.4 (m, 1H), 6.9-7.2 (m, 6H), 5.1 (s, 1H), 3.3-3.4 (m, 1H), 2.9-3.1 (m, 1H), 2.7-2.9 (m, 6H), 1.9-2.2 (q, 2H).

Workup

  1. customThis product was prepared

Sources & evidence

ORD record
ord-7b3557109f2540b4ba31a03dc362f5e0
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

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