Hydrochloric Acid → N-(2-Cyano-4-methylphenyl)-4-piperidone

HRID 842783Notes

Reaction equation

HRID 842783 reaction equation
C1O[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=3[C:18]#[N:19])[CH2:7][CH2:6]2)[O:4]C1C.Cl>CCOCC>[C:18]([C:12]1[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=1[N:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1)#[N:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86757963N-(2-Cyano-4-methylphenyl)-4-piperidone propylene ketal

Product 1

HCID 22615416N-(2-Cyano-4-methylphenyl)-4-piperidone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 29 (549 mg, 2.00 mmol) in ether (20 mL) was treated with 3N aqueous HCl (25 mL). The mixture was stirred at room temperature (24 h). The solvent was removed in vacuo and the residue dissolved in 6N HCl (25 mL) and acetic acid (10 mL). The mixture was stirred at room temperature (3 h). The reaction mixture was neutralized with sodium carbonate solution and the aqueous layer was extracted with three portions of ether. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound (30).

Workup

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

Sources & evidence

ORD record
ord-87f8721a71604261af6e2c1230d3796f
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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