Tryptamine → HCID 3389390, compound

HRID 1837140Notes

Reaction equation

HRID 1837140 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.C(=O)(O)[O-].[Na+].[N+:18]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1F)([O-:20])=[O:19]>O.C(O)C>[N+:18]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[NH: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-:20])=[O:19]

Participants

6

Reactant 3

HCID 1150TryptamineHCID 6264DinitrofluorobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 3389390HCID 3389390, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1 mMole of tryptamine was dissolved in 100 ml of water and the pH was adjusted to pH 8.3 with 2.5 moles of sodium bicarbonate (NaHCO3), A 1.5% solution of 2,4-dinitrofluorobenzene in 200 liters ethanol was added and the mixture was stirred during 2 hours at room temperature. The desired product precipitates out, it is washed and dried. The product is obtained in 90% yield, and TLC (chloroform, silica-gel plates, reveals one yellow spot (Rf=0.84) which is well resolved from the starting materials under the same conditions.

Workup

  1. customThe desired product precipitates out
  2. washit is washed
  3. customdried
  4. customThe product is obtained in 90% yield, and TLC (chloroform, silica-gel plates

Sources & evidence

ORD record
ord-26bb7627f6284229b0e962029411d449
Source dataset
uspto-grants-2004_08
Patent number
US06780884B2

Reaction notes

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