Hydrochloric Acid → HCID 15296935, compound

HRID 487155Notes

Reaction equation

HRID 487155 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl>C(O)C.[Pd]>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]([CH3:19])[CH3:18])=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15290024HCID 15290024, compound

Product 1

HCID 15296935HCID 15296935, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In 100 mi of ethanol was dissolved 5.49 g of the 1-acetyl-4-(4-dimethylaminobenzoyl)piperidine (Compound No. 4) prepared in Example 4, followed by addition of concentrated hydrochloric acid (2 ml). Using 10% palladium-on-carbon as the catalyst, catalytic reduction was carried out at atmospheric temperature and pressure for 48 hours. After completion of the reaction, the solvent was distilled off and the residual oil was dissolved in ethyl acetate (100 ml). The solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and water in that order and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residual oil was subjected to silica gel column chromatography (eluent: methanol:dichloromethane=1:19, v/v) to give 3.9 g of the title compound as a colorless oil.

Workup

  1. customprepared in Example 4
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionthe residual oil was dissolved in ethyl acetate (100 ml)
  5. washThe solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and water in that order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-09c72a2929564c9889aa07ac2466a904
Source dataset
uspto-grants-1994_03
Patent number
US05294625

Reaction notes

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