Ethanol → HCID 19390914, compound

HRID 1645862Notes

Reaction equation

HRID 1645862 reaction equation
C(O)C.[ClH:4].Cl.[N:6]1([C:11]2[CH:24]=[CH:23][C:14]([C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=O)=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1>[Pd].O>[ClH:4].[ClH:4].[N:6]1([C:11]2[CH:12]=[CH:13][C:14]([CH2:15][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:23][CH:24]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 702EthanolHCID 19390858HCID 19390858, compound

Product 1

HCID 19390914HCID 19390914, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

In a solvent mixture of 20 ml of ethanol and 20 ml of water was added 3.33 g of the 4-(4-pyrrolidinobenzoyl)piperidine dihydrochloride (Compound No. 1) prepared in Example 11, followed by addition of 10% palladium-on-carbon, and the catalytic reduction was carried out at atmospheric temperature and pressure for 2 hours. After completion of the reaction, the solvent was distilled off and the residue was dissolved in a saturated aqueous solution of sodium chloride. The solution was made basic by addition of solid sodium hydrogen carbonate and extracted with acetonitrile. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off. After addition of 2N-methanolic hydrochloric acid to the oily residue, the solvent was distilled off and the residue was recrystallized from ethyl ether-methanol to give 0.4 g of colorless crystals melting at 152°-154° C.

Workup

  1. customprepared in Example 11
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionthe residue was dissolved in a saturated aqueous solution of sodium chloride
  5. additionThe solution was made basic by addition of solid sodium hydrogen carbonate
  6. extractionextracted with acetonitrile
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off
  9. additionAfter addition of 2N-methanolic hydrochloric acid to the oily residue
  10. distillationthe solvent was distilled off
  11. customthe residue was recrystallized from ethyl ether-methanol

Sources & evidence

ORD record
ord-854787bbe0af4abb9ce00b63af67af05
Source dataset
uspto-grants-1993_01
Patent number
US05177087

Reaction notes

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