Potassium Carbonate → HCID 69590511, compound

HRID 585556Notes

Reaction equation

HRID 585556 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21]/[CH:22]=[CH:23]/[C:24]([O:26][CH3:27])=[O:25]>CN(C)C=O>[CH3:27][O:26][C:24](=[O:25])[CH:23]=[CH:22][CH2:21][N:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 759941-BenzylpiperazineHCID 53691752-Butenoic acid, 4-bromo-, methyl ester

Product 1

HCID 69590511HCID 69590511, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a ice chilled solution of 1-benylpiperazine (25.0 g, 0.14 moles) in 140 mL dimethylformamide was added potassium carbonate (24.0 g, 1.25 eq.) and methyl 4-bromocrotonate (18.6 mL, 0.99 eq.). The solution was warmed to room temperature and stirred 24 h. The solution was filtered. Water was added and extracted with ethyl acetate. The organics were washed with water twice and brine, dried over sodium sulfate, filtered and evaportated to afford methyl -4-(4-benzylpiperazin-1-yl)but-2-enoate (35.2 g, 92%) as a brown-orange liquid. MS (ESI+) for m/z 275 (M+H)+.

Workup

  1. filtrationThe solution was filtered
  2. additionWater was added
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed with water twice
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-1f6837b09cb344ea81683c6fecd9de0a
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

Loading…