Tryptamine → HCID 201170, compound

HRID 988302Notes

Reaction equation

HRID 988302 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.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:18]=O.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]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:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

7

Reactant 4

HCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 8419VeratraldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 201170HCID 201170, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tryptamine (5.0 g, 0.0312 mol) and 3,4-dimethoxy benzaldehyde (5.7 g, 0.0312 mol) in CH2Cl2 (220 mL) was added TFA (4.5 mL, 0.0584 mol). The deep blue solution was stirred at room temperature for 20 h. The reaction mixture was neutralized with NaHCO3 (4.9 g, 0.0584 mol) in H2O (50 mL) and the organic layer washed with brine (2×100 mL). The reaction mixture was dried with MgSO4 and the solvent evaporated. Product was isolated by column chromatography (silica gel; CH3OH:EtOAc=1:9) as a yellowish oil, which solidified slowly upon standing at room temperature.

Workup

  1. washthe organic layer washed with brine (2×100 mL)
  2. dry with materialThe reaction mixture was dried with MgSO4
  3. customthe solvent evaporated
  4. customProduct was isolated by column chromatography (silica gel; CH3OH:EtOAc=1:9) as a yellowish oil, which
  5. customupon standing at room temperature

Sources & evidence

ORD record
ord-5ed32a2e1e6047e9a249f9275fd9bf16
Source dataset
uspto-grants-2003_10
Patent number
US06635638B2

Reaction notes

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