Benzaldehyde → 1-Phenyl-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 1723796Notes

Reaction equation

HRID 1723796 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(C(F)(F)F)=O.N#N>CCO.C(Cl)(Cl)Cl>[C:15]1([CH:14]2[C:6]3[NH:7][C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5]=3[CH2:4][CH2:3][NH:2]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 947NitrogenHCID 6422Trifluoroacetic acidHCID 67652Tryptamine hydrochloride

Product 1

HCID 1989671-Phenyl-2,3,4,9-tetrahydro-1H-beta-carbolineYield 15.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

1-Phenyl-2,3,4,9-tetrahydro-1H-beta-carboline was prepared by the addition of tryptamine-HCl (500 mg, 2.54 mmol), CHCl3 (20 mL), absolute EtOH (16 mL), benzaldehyde (520 μL, 5.08 mmol), and TFA (1.9 mL, 25.4 mmol) to a N2 purged 50 mL flask. The reaction solution was allowed to stir at ambient temperature for 18 hours and then at 60° C. for 4 hours. The solution was concentrated under reduced pressure, and the crude material was chromatographed (SiO2, 100% hexane to 25% EtOAc) to yield 95 mg of 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline; MS(ESI): 249(MH+).

Workup

  1. custompurged 50 mL flask
  2. waitat 60° C. for 4 hours
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe crude material was chromatographed (SiO2, 100% hexane to 25% EtOAc)

Sources & evidence

ORD record
ord-7d093386c7a64f3ab54f06533ff376a0
Source dataset
uspto-grants-2009_02
Patent number
US07485634B2

Reaction notes

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