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

HRID 1637866Notes

Reaction equation

HRID 1637866 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.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[C:14]1([CH:13]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:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 10340Sodium Carbonate

Product 1

HCID 1989671-Phenyl-2,3,4,9-tetrahydro-1H-beta-carbolineYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tryptamine (15 g, 94.0 mmol) and benzaldehyde (10.9 g, 1.1 equiv.) in DCM (800 mL) was treated with TFA (15 mL, 2 equiv.). The resulting mixture was stirred at rt for one day and then neutralized to pH 7 with a saturated aqueous solution of sodium carbonate. After filtration and concentration to dryness the residue was recrystallized from 2-propanol to give the title compound (11.0 g, 47%) as white crystals. MP: 175-177° C.

Workup

  1. filtrationAfter filtration and concentration to dryness the residue
  2. customwas recrystallized from 2-propanol

Sources & evidence

ORD record
ord-4c40750c8ac64b17af694e362a285422
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

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