Sodium Hydroxide → 3-Dipropylaminomethyl-benzoic acid

HRID 2080767Notes

Reaction equation

HRID 2080767 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[CH:5]=1.[OH-].[Na+]>CO>[CH2:12]([N:11]([CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:18])=[O:2])[CH2:15][CH2:16][CH3:17])[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67103830HCID 67103830, compound

Product 1

HCID 167762183-Dipropylaminomethyl-benzoic acidYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (858 mg) obtained in Example 18-1 was dissolved in methanol (18 ml) and added with a 1 mol/l sodium hydroxide aqueous solution (9.0 ml) and the whole was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in a 1 mol/l hydrochloric acid. After addition of chloroform, the resultant was added with sodium chloride to make the aqueous layer to be a saturated saline solution. The whole was subjected to extraction with chloroform and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was dried under vacuum, thereby obtaining the subject compound (781 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in a 1 mol/l hydrochloric acid
  4. additionAfter addition of chloroform
  5. additionthe resultant was added with sodium chloride
  6. extractionThe whole was subjected to extraction with chloroform
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-c256e3211f604dedb4c83e58768a3a55
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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