Potassium Carbonate → HCID 117942003, compound

HRID 1499200Notes

Reaction equation

HRID 1499200 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4](F)[CH:3]=1.[N:12]1([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:21]([O:20][C:18]([N:12]1[CH2:17][CH2:16][N:15]([C:4]2[CH:3]=[C:2]([Br:1])[CH:10]=[CH:9][C:5]=2[C:6]([OH:8])=[O:7])[CH2:14][CH2:13]1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3026814-Bromo-2-fluorobenzoic acidHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 117942003HCID 117942003, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-bromo-2-fluorobenzoic acid (2 g, 9.1 mmol), benzyl piperazine-1-carboxylate (2.4 g, 10.9 mmol) and K2CO3 (2.5 g, 18.26 mmol) in DMF (40 mL) was stirred at 150° C. for 36 h. The reaction was then cooled to RT and extracted with ethyl acetate, 3 N HCl, brine, dried over Na2SO4, filtered and concentrated in vacuo to provide 2-(4-((benzyloxy) carbonyl)piperazin-1-yl)-4-bromobenzoic acid as yellow oil that was used without further purification.

Workup

  1. temperatureThe reaction was then cooled to RT
  2. extractionextracted with ethyl acetate, 3 N HCl, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a5f54ef07db41b8aa4a9c79582d17c7
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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