Potassium Cyanide → HCID 54536415, compound

HRID 1870251Notes

Reaction equation

HRID 1870251 reaction equation
Br[CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1.[C-:24]#[N:25].[K+]>CS(C)=O>[C:24]([CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1)#[N:25]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 56975661HCID 56975661, compound

Product 1

HCID 54536415HCID 54536415, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
47.5 °C

Procedure

A mixture of (5S)-5-bromomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.83 g), potassium cyanide (0.27 g) and dimethyl sulfoxide (9 ml) is heated with stirring at 45-50° C. for three hours. To the reaction solution is added ice, and the mixture is extracted with ethyl acetate--diethyl ether. The extract is dried over sodium sulfate, and evaporated under reduced pressure to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; n-hexane: ethyl acetate=6:1), and recrystallized from ethyl acetate--n-hexane to give (5R)-5-cyanomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.60 g).

Workup

  1. temperatureis heated
  2. additionTo the reaction solution is added ice
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe extract is dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe resulting residue is purified by silica gel column chromatography (solvent; n-hexane: ethyl acetate=6:1)
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-69087f85f68240c68246d7cd6c46d502
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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