Methyl iodide → HCID 86741154, compound

HRID 1249084Notes

Reaction equation

HRID 1249084 reaction equation
[CH2:1]([C@H:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH2:7][C@@H:6]([C:17]([OH:19])=[O:18])[NH:5]1)[CH2:2][CH3:3].C(N(CC)CC)C.[C:27](=[S:29])=[S:28].[CH3:30]I>CO>[CH2:1]([C@H:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH2:7][C@@H:6]([C:17]([OH:19])=[O:18])[N:5]1[C:27]([S:29][CH3:30])=[S:28])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 762190HCID 762190, compound

Product 1

HCID 86741154HCID 86741154, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1RS,3RS)-cis-n-Propyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (450 mg) is dissolved in 80% methanol (10 ml), and thereto are added triethylamine (350 mg) and carbon disulfide (270 ml). The mixture is stirred at room temperature for 30 minutes, and methyl iodide (490 mg) is added to the mixture. The mixture is stirred at room temperature for 2 hours, and then distilled to remove the solvent. Water is added to the mixture, and the aqueous solution is acidified with 5% HCl, and extracted with ethyl acetate. The extract is washed with water, dried and then distilled to remove the solvent. The residue is treated with aqueous ethanol to give the title compound (350 mg, 59%) as pale yellow powder.

Workup

  1. stirringThe mixture is stirred at room temperature for 2 hours
  2. distillationdistilled
  3. customto remove the solvent
  4. additionWater is added to the mixture
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with water
  7. customdried
  8. distillationdistilled
  9. customto remove the solvent
  10. additionThe residue is treated with aqueous ethanol

Sources & evidence

ORD record
ord-a4f143ac1d704fee9edee32dad97840d
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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