Hydrochloric Acid → 4-(4-Oxopiperidin-1-yl)benzonitrile

HRID 842785Notes

Reaction equation

HRID 842785 reaction equation
C1O[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]C1C.Cl>CCOCC>[C:17]([C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)=[CH:16][CH:15]=1)#[N:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57228643N-(4-Cyanophenyl)-4-piperidone propylene ketal

Product 1

HCID 110198874-(4-Oxopiperidin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 34 (915 mg, 3.54 mmol) in ether (6 mL) was treated with 6N aqueous HCl (25 mL). The mixture was stirred at room temperature (2 d). The solvent was removed in vacuo and the residue dissolved in 3N HCl (25 mL) and acetic acid (20 mL). The mixture was stirred at room temperature (2 h). The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium carbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 4 mm, 10% EtOH-90% CHCl3) afforded the title compound (35).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in 3N HCl (25 mL)
  3. stirringThe mixture was stirred at room temperature (2 h)
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue dissolved in dichloromethane
  6. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  7. washthe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d791415aa9c44db9b016848b5efd37ae
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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