Acetic Acid → HCID 12799869, compound

HRID 1995094Notes

Reaction equation

HRID 1995094 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1>C(O)C.[Pt]=O>[NH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[CH2:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 20489582HCID 20489582, compound

Product 1

HCID 12799869HCID 12799869, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

30 ml of a 10 N aqueous solution of acetic acid are added to a solution containing 7 g of 4-[2-(2-pyridyl)-ethyl]-quinoline in 700 ml of ethanol, then 1.4 g of 82% platinum oxide is added as catalyst. Hydrogenation is effected at 45° C. under a hydrogen pressure equal to the normal pressure (1 bar) for 24 hours, being careful to replace the catalyst used every eight hours by fresh catalyst. At the end of the 24 hours (the quantity of hydrogen absorbed is then 2.9 liters), the catalyst is removed by filtration, the ethanol is evaporated under reduced pressure and the residue is taken up with 200 ml of water. The aqueous phase is extracted with chloroform, then made alkaline with concentrated ammonia and extracted with methylene chloride. The methylene chloride phase is dried over magnesium sulfate and evaporated under reduced pressure. The oily residue (6.3 g) is fixed on a column containing 630 g of silica, then eluted with a 9/1 toluene-diethylamine mixture. 1.9 g are thus isolated of 4-[2-(2-piperidyl)-ethyl]-quinoline.

Workup

  1. customis effected at 45° C. under a hydrogen
  2. customfor 24 hours
  3. customAt the end of the 24 hours (the quantity of hydrogen absorbed
  4. custom2.9 liters), the catalyst is removed by filtration
  5. customthe ethanol is evaporated under reduced pressure
  6. extractionThe aqueous phase is extracted with chloroform
  7. extractionextracted with methylene chloride
  8. dry with materialThe methylene chloride phase is dried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. additioncontaining 630 g of silica
  11. washeluted with a 9/1 toluene-diethylamine mixture

Sources & evidence

ORD record
ord-416c8ac61ecc45c5b3c4c1b36a47f438
Source dataset
uspto-grants-1983_09
Patent number
US04402961

Reaction notes

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