Sodium Carbonate → HCID 19004338, compound

HRID 2225811Notes

Reaction equation

HRID 2225811 reaction equation
C([O:3][C:4](=[O:29])[C:5](=[O:28])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14](=[O:27])[N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[O:27]=[C:14]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)[CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:5](=[O:28])[C:4]([OH:29])=[O:3])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 54295833HCID 54295833, compound

Product 1

HCID 19004338HCID 19004338, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-[2-Oxo-2-(4-phenyl-1-piperazinyl)ethoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.7 g) in methanol (40 mL) was treated with sodium carbonate (0.24 g) in water (6 mL), and the mixture was stirred at room temperature for 1.25 hours. After the methanol was evaporated under reduced pressure, water was added and the solution was acidified with 3N hydrochloric acid, then the aqueous layer was extracted with a dichloromethane-tetrahydrofuran mixture (1:1). The organic layer was dried (MgSO4), evaporated, and the residue was crystallized from acetone to furnish 0.3 g of 4-[2-oxo-2-(4-phenyl-1-piperazinyl)ethoxy]-alpha-oxobenzeneacetic acid, mp 188°-192 ° C.

Workup

  1. customAfter the methanol was evaporated under reduced pressure, water
  2. additionwas added
  3. extractionthe aqueous layer was extracted with a dichloromethane-tetrahydrofuran mixture (1:1)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customthe residue was crystallized from acetone

Sources & evidence

ORD record
ord-11e5920cba7d4f5ab6a68b7f11096c56
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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