Acetic Acid → HCID 12799870, compound

HRID 1995095Notes

Reaction equation

HRID 1995095 reaction equation
C(O)(=O)C.[C:5]1([C:11]2[CH:20]=[C:19]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C.[Pt]=O>[C:5]1([C:11]2[CH:20]=[C:19]([CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][NH:24]3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 20489587HCID 20489587, compound

Product 1

HCID 12799870HCID 12799870, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

4.55 ml of concentrated acetic acid are added to a solution containing 2.5 g of 2-phenyl-4-[2-(2-pyridyl)-ethyl]-quinoline in 250 ml of ethanol, then 0.5 g of 82% platinum oxide is added as catalyst. Hydrogenation is effected at 30° C., under a hydrogen pressure equal to the normal pressure for 6 hours, at the end of which time 700 ml of hydrogen have been absorbed. The catalyst is eliminated by filtration. The ethanol is evaporated under reduced pressure and the residue is taken up with 200 ml of water. The aqueous phase is made alkaline by means of concentrated ammonia, and extracted with methylene chloride. The organic phase is dried over magnesium sulfate and evaporated under reduced pressure. The residue obtained is fixed on a column of 200 g of silica and eluted with a 9/1 toluene-diethylamine mixture. 0.65 g are thus isolated of 2-phenyl-4-[2-(2-piperidyl)-ethyl]-quinoline in the form of an oil. This compound is dissolved in acetone and converted, by addition of hydrochloric acid, to its dihydrochloride, which melts at 200° C.

Workup

  1. customis effected at 30° C., under a hydrogen
  2. customfor 6 hours
  3. customat the end of which time 700 ml of hydrogen have been absorbed
  4. filtrationThe catalyst is eliminated by filtration
  5. customThe ethanol is evaporated under reduced pressure
  6. extractionextracted with methylene chloride
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue obtained
  10. washeluted with a 9/1 toluene-diethylamine mixture

Sources & evidence

ORD record
ord-8317a0fb00b84270b315c1cd570ade2f
Source dataset
uspto-grants-1983_09
Patent number
US04402961

Reaction notes

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