Potassium Cyanide → tert-butyl 4-[4-[(Z)-C-cyano-N-hydroxycarbonimidoyl]phenyl]piperazine-1-carboxylate

HRID 1744120Notes

Reaction equation

HRID 1744120 reaction equation
[OH:1]/[N:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[O-]Cl.[Na+].[C-:26]#[N:27].[K+]>C(Cl)Cl.[Cl-].[Na+].O>[C:26](/[C:3](=[N:2]\[OH:1])/[C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1)#[N:27]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 22236181tert-butyl 4-[4-[(E)-hydroxyiminomethyl]phenyl]piperazine-1-carboxylateHCID 23665760Sodium Hypochlorite

Product 1

HCID 22236172tert-butyl 4-[4-[(Z)-C-cyano-N-hydroxycarbonimidoyl]phenyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To tert-butyl 4-{4-[(E)-(hydroxyimino)methyl]phenyl}piperazine-1-carboxylate (1.593 g, 5.22 mmol) in CH2Cl2 (25 mL) was gradually added Javex (approx. 10% NaOCl, 19.5 mL,.26.1 mmol) and the reaction mixture stirred for 1 hour. Potassium cyanide (3.4 g, 52.2 mmol) was added and the reaction stirred for 1 hour. The reaction was poured into brine and the product extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo with silica gel (to pre-adsorb product on silica gel) and purified by flash chromatography over silica gel (EtOAc/Hex, 1/1) to afford tert-butyl 4-(4-[(Z)-cyano(hydroxyimino)methyl]phenyl}piperazine-1-carboxylate.

Workup

  1. stirringthe reaction stirred for 1 hour
  2. extractionthe product extracted with EtOAc (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo with silica gel (to pre-adsorb product on silica gel)
  5. custompurified by flash chromatography over silica gel (EtOAc/Hex, 1/1)

Sources & evidence

ORD record
ord-87952f6a625f43f48b637420bc7ca254
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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