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

HRID 990721Notes

Reaction equation

HRID 990721 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.[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]=O)=[CH:21][C:16]=2[CH2:15][CH2:14]1.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl>[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([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:21][C:16]=2[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 7359012,3-Dihydrobenzofuran-5-carboxaldehyde

Product 1

HCID 111090451-(2,3-dihydro-5-benzofuranyl)-2,3,4,9-tetrahydro-1H-beta-carbolineYield 80%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared using a two-step procedure. A solution of tryptamine (32.4 g, 0.2 mol) and 2,3-dihydrobenzofuran-5-carboxaldehyde (30.0 g, 1 eq.) in toluene (1 L) was heated under reflux for 4 hours. After removal of 4 mL of water and evaporation of toluene, the residue was dissolved in CH2Cl2 (1 L) in the presence of TFA (31 mL, 2 eq.). The resulting mixture was stirred at rt for 16 hours. Then, 1 L of a saturated aqueous solution of sodium bicarbonate (NaHCO3) was added. After extraction with CH2Cl2 and drying over magnesium sulfate (MgSO4), the organic solution was evaporated in vacuo. Recrystallization from CH2Cl2/iPr2O (diisopropyl ether) (2:30) gave the title compound as white crystals in an 80% yield. 1H NMR (CDCl3), δ7.6 (s, 1H), 7.5-7.6 (m, 1H), 7-7.3 (m, 5H), 6.7-6.75 (d, 1H), 5.1 (s, 1H), 4.5-4.6 (t, 2H), 3.3-3.45 (m, 1H), 3.05-3.2 (t, 3H), 2.7-3 (m, 2H).

Workup

  1. customThis compound was prepared
  2. temperatureunder reflux for 4 hours
  3. customAfter removal of 4 mL of water and evaporation of toluene
  4. extractionAfter extraction with CH2Cl2
  5. dry with materialdrying over magnesium sulfate (MgSO4)
  6. customthe organic solution was evaporated in vacuo
  7. customRecrystallization from CH2Cl2/iPr2O (diisopropyl ether) (2:30)

Sources & evidence

ORD record
ord-4155bd8583ab402da3d0ed29dd7ed828
Source dataset
uspto-grants-2002_10
Patent number
US06462047B1

Reaction notes

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