Acetic Anhydride → 4-(1-Acetylpiperidin-4-yl)benzoic acid

HRID 1264318Notes

Reaction equation

HRID 1264318 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>N1C=CC=CC=1>[C:16]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 180024624-(Piperidin-4-yl)benzoic acid

Product 1

HCID 186177774-(1-Acetylpiperidin-4-yl)benzoic acidYield 49.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-piperidin-4-yl)-benzoic acid (102 mg, 0.5 mmol, reference example 109) dissolved in pyridine (2 mL) was added acetic anhydride (255 mg, 2.5 mmol) and the reaction stirred overnight at room temperature. The reaction was concentrated in vacuo and residual pyridine partially removed by azeotroping with dichloromethane/methanol 1:1. The crude product was then washed with dichlormethane and the solvent decanted to yield a white solid residue (61 mg, 49%) 4-(1-acetyl-piperidin-4-yl)-benzoic acid. 1H NMR (CD3OD): δ 7.89 (d, 2H); 7.27 (d, 2H); 4.65 (d, 1H); 4.03 (d, 1H); 3.21 (dt, 2H); 2.68-2.88 (m, 2H); 1.93 (s, 3H); 1.85-2.04 (m, 2H); 1.50-1.75 (m, 3H). MS m/z 248 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo and residual pyridine
  2. custompartially removed
  3. customby azeotroping with dichloromethane/methanol 1:1
  4. washThe crude product was then washed with dichlormethane
  5. customthe solvent decanted

Sources & evidence

ORD record
ord-3b7f576ffa4d4146b0abe1dd883e5fba
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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