5-Methoxytryptamine → HCID 18794245, compound

HRID 1004055Notes

Reaction equation

HRID 1004055 reaction equation
[C:1]([CH:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][C:9]#[N:10])([O:3]CC)=O.[CH3:16][O:17][C:18]1[CH:29]=[C:28]2[C:21]([NH:22][CH:23]=[C:24]2[CH2:25][CH2:26]N)=[CH:20][CH:19]=1>C(O)(=O)C.[Pd]>[CH3:16][O:17][C:18]1[CH:29]=[C:28]2[C:21](=[CH:20][CH:19]=1)[NH:22][C:23]1[CH:9]3[CH2:8][CH2:7][CH:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:1](=[O:3])[N:10]3[CH2:26][CH2:25][C:24]2=1

Participants

5

Reactant 2

HCID 18335-MethoxytryptamineHCID 87005Diethyl (2-cyanoethyl)malonate

Product 1

HCID 18794245HCID 18794245, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4,4-Dicarbethoxybutyronitrile (1.2 g)and palladium-on-charcoal (0.6 g) are successively added to 5-methoxytryptamine (693 mg) dissolved in acetic acid. The mixture is stirred under a hydrogen atmosphere for 48 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 ethyl 9-methoxy-4-oxo-1,2,3,4,6,7,12,12b-octahydropyrido[2,1 -a]-(3-carboline-3-carboxylate precipitates and is recovered by simple filtration (35% 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-a453edc0b6ef47dca762be08960d69b5
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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