Dichloromethane → 2-Acetoxy-5-(piperidin-1-yl)benzoic acid

HRID 454485Notes

Reaction equation

HRID 454485 reaction equation
C(Cl)Cl.[C:4](OC(=O)C)(=[O:6])[CH3:5].[OH:11][C:12]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>N1C=CC=CC=1>[C:4]([O:11][C:12]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 669907452-Hydroxy-5-(piperidin-1-yl)benzoic acid

Product 1

HCID 669905182-Acetoxy-5-(piperidin-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methylene chloride (9.0 mL), pyridine (0.82 mL), and acetic anhydride (0.46 mL) were sequentially added to the obtained 2-hydroxy-5-(piperidin-1-yl)benzoic acid (0.90 g), followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, and the resulting mixture was washed with water and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration to obtain 0.55 g of 2-acetoxy-5-(piperidin-1-yl)benzoic acid as a light yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiona 10% aqueous solution of citric acid and ethyl acetate were added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washthe resulting mixture was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  8. additionwas added to the obtained residue
  9. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-4e5be5f8791145e980a4df123de1106b
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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