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

HRID 1417474Notes

Reaction equation

HRID 1417474 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(Cl)Cl.CO>C(O)(=O)C>[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 887MethanolHCID 1150TryptamineHCID 6344Dichloromethane

Product 1

HCID 1989671-Phenyl-2,3,4,9-tetrahydro-1H-beta-carbolineYield 661.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.0 g (6.24 mmol) of tryptamine and 0.73 g (0.87 mmol) of benzaldehyde in 10 ml of acetic acid was refluxed for 3 hours. After completion of the reaction, the solvent was distilled off, and the residue was made alkaline by the addition of a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and then the solvent was removed by evaporation under reduced pressure to give 1.82 g of a crude mixture. The resulting residue was subjected to column chromatography using 35 g of silica gel with a 9:1 by volume mixture of methylene chloride and methanol as the eluent, to yield 1.43 g (92%) of the title compound. The product was subsequently recrystallized from dichloroethane and hexane to yield 0.72 g of pale yellowish brown crystals.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. additionby the addition of a saturated aqueous solution of sodium hydrogencarbonate
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed by evaporation under reduced pressure
  9. customto give 1.82 g of a crude mixture

Sources & evidence

ORD record
ord-a229b11d911f4800bb2cc8a823ac0b8c
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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