Tryptamine → HCID 728709, compound

HRID 1095547Notes

Reaction equation

HRID 1095547 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:13]1([N:19]=[C:20]=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(C)=O.C(N(CC)CC)C.C(Cl)(Cl)Cl.CO>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][NH:1][C:20]([NH:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:21])=[CH:5]1

Participants

6

Reactant 2

HCID 1150Tryptamine2×HCID 7672Phenyl isocyanate

Product 1

HCID 728709HCID 728709, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8471TriethylamineSolventHCID 21584188Chloroform methanolSolvent

Procedure

Tryptamine (1.04 g, 6.5 mmol) was dissolved in a mixture of acetone (20 ml) and triethylamine (1 ml) under a nitrogen atmosphere. Phenyl isocyanate (852 mg, 7.15 mmol, 0.78 ml) was swiftly added dropwise at 0° C. and the mixture was then subsequently stirred for 2 h, while cooling with ice, and at RT overnight. A subsequent TLC in chloroform/methanol 20:1 showed only small amounts still of tryptamine. The mixture was concentrated i. vac. The residue obtained was purified by flash chromatography with 100 g of silica gel and chloroform/methanol 50:1→9:1.

Workup

  1. temperaturewhile cooling with ice
  2. customat RT
  3. customovernight
  4. concentrationThe mixture was concentrated i
  5. customThe residue obtained
  6. customwas purified by flash chromatography with 100 g of silica gel and chloroform/methanol 50:1→9:1

Sources & evidence

ORD record
ord-3e566852bd60425bbd24624ab78572be
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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