Acetic Acid → (4-Hydroxy-phenyl)-piperidin-4-yl-methanone

HRID 1295574Notes

Reaction equation

HRID 1295574 reaction equation
Cl.C[O:3][C:4]1[CH:17]=[CH:16][C:7]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1.C(O)(=O)C>Br.C([O-])(O)=O.[Na+]>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 27405874-(4-Methoxybenzoyl)piperidine hydrochloride

Product 1

HCID 13180304(4-Hydroxy-phenyl)-piperidin-4-yl-methanoneYield 73.3%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-(4-methoxybenzoyl)piperidine hydrochloride (3.0 g, 11.7 mmol), in 48% HBr (aq) (16 mL), and acetic acid (16 mL) was heated at reflux for 48 h. The reaction mixture was evaporated to dryness in vacuo to give an off-white solid which was suspended in saturated NaHCO3 (aq). The resulting precipitate was collected by filtration, washed with water, and dried to give the title compound (1.76 g, 73%) as an off-white solid.

Workup

  1. temperatureat reflux for 48 h
  2. customThe reaction mixture was evaporated to dryness in vacuo
  3. customto give an off-white solid which
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-11b7d1303fb3447783202a163ba54b3e
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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