Tryptamine → HCID 930813, compound

HRID 1095546Notes

Reaction equation

HRID 1095546 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.[CH2:13]([N:20]=[C:21]=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(C)=O.C(N(CC)CC)C.C(Cl)(Cl)Cl.CO>[CH2:13]([NH:20][C:21]([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:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 1150Tryptamine2×HCID 76639Benzyl isocyanate

Product 1

HCID 930813HCID 930813, 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. Benzyl isocyanate (952 mg, 7.15 mmol, 0.88 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 for 2 h. 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 20:1→9:1→4:1.

Workup

  1. temperaturewhile cooling with ice
  2. waitat RT for 2 h
  3. concentrationThe mixture was concentrated i
  4. customThe residue obtained
  5. customwas purified by flash chromatography with 100 g of silica gel and chloroform/methanol 20:1→9:1→4:1

Sources & evidence

ORD record
ord-43c35dbf00eb4002813ae4adf4f55845
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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