1-Piperazinecarboxylic acid, ethyl ester → HCID 18940681, compound

HRID 355739Notes

Reaction equation

HRID 355739 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])[CH3:20]>CS(C)=O>[CH2:19]([O:21][C:22]([N:24]1[CH2:25][CH2:26][N:27]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:28][CH2:29]1)=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 18940681HCID 18940681, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 4-fluorobenzoate (0.93 ml, 6.3 mmol), anhydrous potassium carbonate (0.96 g, 7.0 mmol), ethoxycarbonyl piperazine (0.92 ml, 6.3 mmol)and dry DMSO (30 ml) were heated under dry conditions at 90° C. for 72h. The mixture was partitioned between ethyl acetate and water, dried (sodium sulphate) and evaporated to dryness under reduced pressure. The product was purified by flash column chromatography on silica eluting with 10%MeOH/chloroform to afford the title compound as an oil (1.35 g, 70%).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialdried (sodium sulphate)
  3. customevaporated to dryness under reduced pressure
  4. customThe product was purified by flash column chromatography on silica eluting with 10%MeOH/chloroform

Sources & evidence

ORD record
ord-2719902cde5a494fb69d32b600ea44e3
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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