Potassium Carbonate → tert-butyl 4-[4-[(E)-hydroxyiminomethyl]phenyl]piperazine-1-carboxylate

HRID 1744119Notes

Reaction equation

HRID 1744119 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)=O.C([O-])([O-])=O.[K+].[K+].Cl.[NH2:29][OH:30]>CCO.O>[OH:30]/[N:29]=[CH:1]/[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 2795509Tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylate

Product 1

HCID 22236181tert-butyl 4-[4-[(E)-hydroxyiminomethyl]phenyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylate (3.89 g, 13.41 mmol, prepared as described in Example 10) and K2CO3 (1.02 g, 7.38 mmol) in EtOH (50 mL) was added hydroxylamine hydrochloride (1.4 g, 20.1 mmol) in water (saturated, approx. 2 mL) and the reaction mixture stirred overnight. The reaction was filtered, concentrated in vacuo, water was added and the product filtered to afford tert-butyl 4-{4-[(E)-(hydroxyimino)methyl]phenyl}piperazine-1-carboxylate.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo, water
  3. additionwas added
  4. filtrationthe product filtered

Sources & evidence

ORD record
ord-a24cf33f4a6c4e0ca12136bc80f2f7ef
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

Loading…