Potassium Carbonate → HCID 60043433, compound

HRID 1437230Notes

Reaction equation

HRID 1437230 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]Br.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:4][CH2:3][O:2][CH3:1])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 60043433HCID 60043433, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromoethyl methyl ether (0.94 mL) was added dropwise to a suspension of piperazine-4-carboxylic acid tert-butyl ester (1.87 g) and potassium carbonate (1.38 g) in N,N-dimethylformamide (20 mL) at room temperature, and the resultant mixture was stirred at 60° C. for 24 hours. The reaction mixture was partitioned by use of ice-water and ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as an oily product (1.39 g, 57%).

Workup

  1. customThe reaction mixture was partitioned by use of ice-water and ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate anhydrate
  4. filtrationfollowed by filtration
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-6d60ac5276274234a68b423d9fef4928
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

Loading…