Hydrochloric Acid → HCID 66657833, compound

HRID 420574Notes

Reaction equation

HRID 420574 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([O:12][CH2:13][CH2:14][N:15]2[CH:20]([CH3:21])[CH2:19][N:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][C:16]2([C:29](=[O:31])[NH2:30])[CH3:28])[CH:6]=1.[OH-].[Na+].Cl>O1CCCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:32])=[O:2])=[CH:6][C:7]=1[O:12][CH2:13][CH2:14][N:15]1[CH:20]([CH3:21])[CH2:19][N:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][C:16]1([C:29](=[O:31])[NH2:30])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66657803HCID 66657803, compound

Product 1

HCID 66657833HCID 66657833, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [4-chloro-3-[2-(2,6-dimethyl-4-phenyl carbamoyl piperazine-1-yl)ethoxy]phenyl]acetic acid methyl ester (50 mg), 2N sodium hydroxide (0.1 mL) and tetrahydrofuran (1 mL) was stirred at room temperature for 4 hours. After neutralizing with 2N hydrochloric acid, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel to give the title compound (18 mg). Yield: 37%.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-845a99e8a82b418299f678bc6b9d6142
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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