5-Methoxytryptamine → HCID 18794211, compound

HRID 1004056Notes

Reaction equation

HRID 1004056 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7](=[O:11])OCC)=[O:5])#[N:2].[CH3:12][O:13][C:14]1[CH:25]=[C:24]2[C:17]([NH:18][CH:19]=[C:20]2[CH2:21][CH2:22]N)=[CH:16][CH:15]=1>C(O)(=O)C.[Pd]>[CH3:12][O:13][C:14]1[CH:25]=[C:24]2[C:17](=[CH:16][CH:15]=1)[NH:18][C:19]1[CH:1]3[CH2:3][C:4](=[O:5])[NH:6][C:7](=[O:11])[N:2]3[CH2:22][CH2:21][C:20]2=1

Participants

5

Reactant 2

HCID 18335-MethoxytryptamineHCID 23112N-Cyanoacetylethylcarbamate

Product 1

HCID 18794211HCID 18794211, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl cyanoacetylcarbamate (156 mg) and palladium-on-charcoal (0.6 g) are successively added to 5-methoxytryptamine (119 mg) dissolved in acetic acid. The mixture is stirred under a hydrogen atmosphere for 72 h. The medium is then filtered and the palladium is washed with a chloroform/methanol mixture. After evaporation of the solvent, the crude product obtained, dissolved in toluene, is refluxed overnight. The 9-methoxy-1,2,3,4,6,7,12,12b-octahydropyrimido[6,1-a]-β-carboline-2,4-dione precipitates and is recovered by simple filtration (40% yield).

Workup

  1. filtrationThe medium is then filtered
  2. washthe palladium is washed with a chloroform/methanol mixture
  3. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-bb4ad15c30a1435c80adde0bba495744
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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