Hydrochloric Acid → HCID 13561975, compound

HRID 1249064Notes

Reaction equation

HRID 1249064 reaction equation
[CH2:1]([N:8]1[C:20]2[CH2:19][NH:18][C@@H:17]([C:21]([OH:23])=[O:22])[CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:26]I.Cl.[C:29](=[S:31])=[S:30]>CS(C)=O.O>[CH2:1]([N:8]1[C:20]2[CH2:19][N:18]([C:29]([S:31][CH3:26])=[S:30])[C@@H:17]([C:21]([OH:23])=[O:22])[CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 13562005HCID 13562005, compound

Product 1

HCID 13561975HCID 13561975, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

(3R)-9-Benzyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1.225 g) is dissolved in dimethylsulfoxide (20 ml) and thereto are added 10N NaOH (0.8 ml) and carbon disulfide (0.24 ml). The mixture is stirred at room temperature for 10 minutes and thereto is added dropwise methyl iodide (0.29 ml). The mixture is stirred at room temperature for 20 minutes and thereto is added water (100 ml). The mixture 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 purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=90:5:1) to give the title compound (0.89 g, 52%) as pale yellow powder.

Workup

  1. stirringThe mixture is stirred at room temperature for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=90:5:1)

Sources & evidence

ORD record
ord-6946d3fdf6bf4c60bafd7d241f9de9c5
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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