Hydrogen Peroxide → 1,1-Dimethylethyl 4-(2-amino-1,1-dimethyl-2-oxoethyl)-1-piperazinecarboxylate

HRID 2403404Notes

Reaction equation

HRID 2403404 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:17]#[N:18])([CH3:16])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:20].[K+].[K+].OO>CS(C)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:17](=[O:20])[NH2:18])([CH3:16])[CH3:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 57420353tert-Butyl 4-(2-cyanopropan-2-yl)piperazine-1-carboxylate

Product 1

HCID 574203541,1-Dimethylethyl 4-(2-amino-1,1-dimethyl-2-oxoethyl)-1-piperazinecarboxylateYield 410.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-(cyano-dimethyl-methyl)-piperazine-1-carboxylic acid tert-butyl ester (1 g) and K2CO3 (100 mg) in dry DMSO (20 mL) at 0° C. was added a 27.5% hydrogen peroxide (2 mL) dropwise. The resulting mixture was heated at 40° C. overnight then diluted with water give a solid. This was collected, washed and dried to give 4-(1-carbamoyl-1-methyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (806 mg). Subsequent treatment with 2M HCl in ether gave 2-piperazin-1-yl-isobutyramide dihydrochloride (100%).

Workup

  1. customgive a solid
  2. customThis was collected
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-b10c24e273044ef7b1713b5753b144c5
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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