Acetic Acid → HCID 20258988, compound

HRID 434674Notes

Reaction equation

HRID 434674 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([F:18])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([CH3:19])=[N:13]3)[CH2:4][CH2:3]1.C(O)(=O)C>[C].[Pd].C(OCC)(=O)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([F:18])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH2:10][CH2:11][CH:12]([CH3:19])[NH:13]3)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 20258989HCID 20258989, compound

Product 1

HCID 20258988HCID 20258988, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Hydroxy-1-piperidyl)-6-fluoroquinaldine (3.7 g) was dissolved in a mixed solvent consisting of 100 ml of acetic acid and 10 ml of ethyl acetate, and 1 g of 5% palladium-carbon was added to the mixture which then was placed in a vitrified autoclave. The reaction mixture was stirred at room temperature under a hydrogen gas pressure of 5 kg/cm2 for 3 hours. After removing hydrogen gas the reaction mixture was taken out. After removing the catalyst, the content was concentrated to dryness, dissolved in 100 ml of chloroform and neutralized with 50 ml of an aqueous 5% sodium hydroxide solution. After separation and washing with 100 ml of water twice, the chloroform layer was dried and concentrated to dryness. To the residue were added 20 ml of hexane and 0.5 g activated carbon and the mixture was heated to dissolve. After removing activated carbon by filtration the hexane layer was cooled to precipitate crystals which then were collected to give 3.4 g of 5-(4-hydroxy-1-piperidyl)-6-fluoro-1,2,3,4-tetrahydroquinaldine.

Workup

  1. additionwas added to the mixture which
  2. customAfter removing hydrogen gas the reaction mixture
  3. customAfter removing the catalyst
  4. concentrationthe content was concentrated to dryness
  5. dissolutiondissolved in 100 ml of chloroform and neutralized with 50 ml of an aqueous 5% sodium hydroxide solution
  6. customAfter separation
  7. washwashing with 100 ml of water twice
  8. dry with materialthe chloroform layer was dried
  9. concentrationconcentrated to dryness
  10. additionTo the residue were added 20 ml of hexane and 0.5 g
  11. temperaturethe mixture was heated to dissolve
  12. customAfter removing activated carbon
  13. filtrationby filtration the hexane layer
  14. temperaturewas cooled
  15. customto precipitate crystals which
  16. customthen were collected

Sources & evidence

ORD record
ord-ce62842850494edcbf092181fc608619
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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