1-Acetyl-4-{[(4-chlorophenyl)methyl]oxy}piperidine → 4-{[(4-Chlorophenyl)methyl]oxy}piperidine

HRID 1727208Notes

Reaction equation

HRID 1727208 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)(=O)C>CO.[OH-].[Na+]>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][O:10][CH:7]2[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]2)=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 690562981-Acetyl-4-{[(4-chlorophenyl)methyl]oxy}piperidine

Product 1

HCID 131944244-{[(4-Chlorophenyl)methyl]oxy}piperidineYield 62.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-acetyl-4-{[(4-chlorophenyl)methyl]oxy}piperidine (Preparation 99, 11 g, 41.1 mmol) in methanol (50 ml) and sodium hydroxide solution (5 M, 30 ml) were refluxed on a steam bath for 10 h. After cooling, methanol was removed and the remaining solution was extracted with petroleum ether (40-60, 3×30 ml). The organic extracts were dried (Na2SO4) and concentrated in vacuo to give an white solid (5.8 g, 62%). A portion was recrystallised from petroleum ether to give needle crystals (3 g).

Workup

  1. temperatureAfter cooling
  2. custommethanol was removed
  3. extractionthe remaining solution was extracted with petroleum ether (40-60, 3×30 ml)
  4. dry with materialThe organic extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc942aec95c5456d88f45b261f17ecd3
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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