Potassium Cyanide → HCID 68507112, compound

HRID 1808344Notes

Reaction equation

HRID 1808344 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][N:16]([S:20]([C:23]3[C:28]([CH3:29])=[CH:27][C:26]([O:30][CH3:31])=[CH:25][C:24]=3[CH3:32])(=[O:22])=[O:21])[CH2:17]2)=[CH:12][CH:11]=1)(=O)=O>CCO.O.C(OCC)(=O)C>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([CH3:32])[C:23]([S:20]([N:16]2[CH2:15][CH2:14][C:13]3[C:18](=[CH:19][C:10]([CH2:9][C:1]#[N:2])=[CH:11][CH:12]=3)[CH2:17]2)(=[O:22])=[O:21])=[C:28]([CH3:29])[CH:27]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 86645317HCID 86645317, compound

Product 1

HCID 68507112HCID 68507112, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 19096565Water ethanolSolvent

Procedure

KCN (2.73 mmol, 1.2 equiv.) was added to a solution of (2-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)methyl methanesulfonate (2.28 mmol, 1 equiv.) in EtOH/water (10 ml), and the mixture was refluxed for 24 h. The reaction mixture was then cooled and diluted with ethyl acetate. Extraction with sat. FeSO4 solution, water and sat. NaCl solution was carried out, and the organic phase was dried over Na2SO4 and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel). Yield: 71%

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. temperatureThe reaction mixture was then cooled
  3. extractionExtraction with sat. FeSO4 solution, water and sat. NaCl solution
  4. dry with materialthe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-3cb0442811a34af18dd272b0338ecbbf
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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