Hydrochloric Acid → [2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl-4-piperidone

HRID 2300303Notes

Reaction equation

HRID 2300303 reaction equation
C1O[C:4]2([CH2:9][CH2:8][N:7]([CH2:10][C:11]3[CH:16]=[CH:15][N:14]=[C:13]([C:17]4[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=4)[CH:12]=3)[CH2:6][CH2:5]2)[O:3]C1.Cl.[OH-].[Na+]>C1COCC1>[CH3:24][O:23][C:21]1[CH:22]=[C:17]([C:13]2[CH:12]=[C:11]([CH2:10][N:7]3[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]3)[CH:16]=[CH:15][N:14]=2)[CH:18]=[C:19]([O:27][CH3:28])[C:20]=1[O:25][CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 213388351-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-4-piperidone ethylene ketal

Product 1

HCID 22557811[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl-4-piperidone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-4-piperidone ethylene ketal (19.0 g) in THF (200 mL) was added 1 M hydrochloric acid (200 mL). The mixture was stirred at 90° C. overnight, then neutralized with 2 M sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. The residual oil was applied to a column of silica gel using chloroform-methanol (40:1) as an eluent. Fractions containing the product were collected and evaporated to give the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. additionFractions containing the product
  6. customwere collected
  7. customevaporated

Sources & evidence

ORD record
ord-2ee7c1ccd0674770872d210fe899fd0b
Source dataset
uspto-grants-2002_12
Patent number
US06498169B1

Reaction notes

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