Sodium Hydroxide → 1-Benzyl-3-methyl-4-piperidone

HRID 362549Notes

Reaction equation

HRID 362549 reaction equation
BrCC(N1C[CH2:9][N:8]([C:11](=O)[C:12]2[CH:17]=[C:16](C)[CH:15]=[C:14](C)[CH:13]=2)[CH2:7][CH:6]1[C:21]1[CH:26]=[CH:25]C(Cl)=C(Cl)C=1)=O.Cl.[O:30]1CCOCC1.[OH-].[Na+]>C(Cl)Cl.O>[CH2:11]([N:8]1[CH2:7][CH2:6][C:21](=[O:30])[CH:26]([CH3:25])[CH2:9]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 10277726(+,-)-Bromoacetyl-2-(3,4-dichlorophenyl)-4-(3,5-dimethylbenzoyl)piperazineHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 5609651-Benzyl-3-methyl-4-piperidone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 3 (Ar2 =3,4-dichlorophenyl) (16 g, 28.49 mmol) in CH2Cl2 (142.5 mL) at 0° C. was added 4N HCl-dioxane solution (71.24 mL, 284.9 mmol) through a dropping funnel. The reaction was gradually warmed up to RT and stirred for 4 h. After completion the solvents were evaporated to give a light yellow solid which was dissolved in H2O (400 mL) and brought to pH 10 with 1N NaOH. The product was extracted from basic aqueous solution with CH2Cl2 (200 mL, 4×), dried over MgSO4, filtered and concentrated to give compound 4 (Ar2 =3,4-dichlorophenyl) as a light yellow solid (12.5 g, 27.09 mmol, 95%). FAB MS [M+1]+ 35 Cl 461.1 Compound 4 was the key intermediate which was used to couple with various aromatic acid for the synthesis of many compounds.

Workup

  1. customAfter completion the solvents were evaporated
  2. customto give a light yellow solid which
  3. extractionThe product was extracted from basic aqueous solution with CH2Cl2 (200 mL, 4×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-726ed117681d403b90513e13e7bca72a
Source dataset
uspto-grants-1999_02
Patent number
US05869488

Reaction notes

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