Sodium Cyanide → HCID 22710704, compound

HRID 352818Notes

Reaction equation

HRID 352818 reaction equation
Br[CH2:2][CH2:3][CH:4]1[CH2:9][N:8]([S:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([Cl:23])[CH:19]=3)[CH:14]=2)(=[O:12])=[O:11])[CH2:7][CH2:6][N:5]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].[C-:31]#[N:32].[Na+]>CN(C)C=O>[C:27]([O:26][C:24]([N:5]1[CH2:6][CH2:7][N:8]([S:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([Cl:23])[CH:19]=3)[CH:14]=2)(=[O:12])=[O:11])[CH2:9][CH:4]1[CH2:3][CH2:2][C:31]#[N:32])=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 22709907HCID 22709907, compound

Product 1

HCID 22710704HCID 22710704, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (20 ml) was dissolved 2-(2-bromoethyl)-1-(tert-butoxycarbonyl)-4-[(6-chloronaphthalen -2-yl)sulfonyl]piperazine (980 mg), followed by the addition of sodium cyanide (102 mg). The resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue and the resulting mixture was washed with water and saturated aqueous NaCl solution, each once. The organic layer thus extracted was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (842 mg) was obtained as a colorless foam.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe resulting mixture was washed with water and saturated aqueous NaCl solution
  4. extractionThe organic layer thus extracted
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent, whereby the title compound (842 mg)
  8. customwas obtained as a colorless foam

Sources & evidence

ORD record
ord-2503e1c3e7354c3eb2841a9c1a495109
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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