Water → HCID 86741149, compound

HRID 1249059Notes

Reaction equation

HRID 1249059 reaction equation
[CH3:1][C@H:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][C@H:4]([C:15]([OH:17])=[O:16])[NH:3]1.O.C(N(CC)CC)C.[CH3:26]I.[C:28](=[S:30])=[S:29]>CO>[CH3:1][C@H:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][C@H:4]([C:15]([OH:17])=[O:16])[N:3]1[C:28]([S:30][CH3:26])=[S:29]

Participants

7

Reactant 5

HCID 962WaterHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 675100HCID 675100, compound

Product 1

HCID 86741149HCID 86741149, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1RS,3SR)-trans-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1.15 g) is dissolved in methanol (30 ml)--water (3 ml) and thereto are added triethylamine (1.9 g) and carbon disulfide (912 mg). The mixture is stirred at room temperature for 20 minutes, and to the mixture is added methyl iodide (1.7 g) and the mixture is stirred at room temperature for 2 hours and then distilled under reduced pressure to remove the solvent. To the residue is added water, and the aqueous solution is acidified with 10% HCl and extracted with ethyl acetate. The extract is washed with water, dried and distilled to remove the solvent. The residue is recrystallized from aqueous ethanol to give the title compound (1.13 g, 70.6%) as colorless needles, m.p. 173°-176° C.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. distillationdistilled under reduced pressure
  3. customto remove the solvent
  4. additionTo the residue is added water
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with water
  7. customdried
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe residue is recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-dac020288e414dfda4e1a56fba568a52
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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