Acetyl chloride → 2-Methoxy-4-(1-acetyl-4-piperidyloxy)benzoic acid

HRID 128584Notes

Reaction equation

HRID 128584 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27]>C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:26](=[O:28])[CH3:27])[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471Triethylamine2×HCID 189141672-Methoxy-4-(4-piperidyloxy)benzoic acid

Product 1

HCID 189141452-Methoxy-4-(1-acetyl-4-piperidyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxy-4-(4-piperidyloxy)benzoic acid (0.6 g, 2.09 mmol) was stirred in THF (10 ml) and treated with triethylamine (0.29 ml, 0.21 g, 2.08 mmol), followed by acetyl chloride (0.18 ml, 0.2 g, 2.5 mmol) and an additional 0.35 ml of triethylamine. The mixture was stirred at ambient temperature for 18 hours, then concentrated in vacuo. The residue was partitioned between aqueous sodium bicarbonate and ethyl acetate. The ethyl acetate layer was extracted with sodium bicarbonate solution. The combined sodium bicarbonate layers were acidified with 1N HCl and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to give 2-methoxy-4-(1-acetyl-4-piperidyloxy)benzoic acid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between aqueous sodium bicarbonate and ethyl acetate
  3. extractionThe ethyl acetate layer was extracted with sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-720351c3d82047af9d81978a72b27c58
Source dataset
uspto-grants-1995_11
Patent number
US05464788

Reaction notes

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