Piperidine → 5-Piperidinoacetyl-8-hydroxycarbostyril

HRID 2397560Notes

Reaction equation

HRID 2397560 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)=[O:4].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C1C=CC=CC=1>[N:17]1([CH2:2][C:3]([C:5]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]3[C:6]=2[CH:7]=[CH:8][C:9](=[O:16])[NH:10]3)=[O:4])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 131952785-Piperidinoacetyl-8-hydroxycarbostyril

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10 g of 5-chloroacetyl-8-hydroxycarbostyril (IV) prepared in Example 4 or 8 was suspended in 50 ml of benzene, and 10 ml of piperidine (III) was added to the suspension followed by allowing the mixture to react while heating under refluxing and stirring for 6 hours. The reaction mixture was filtered to recover the reaction product which was then washed with benzene and then with 50 ml of isopropanol. The resulting insoluble material was dissolved in 150 ml of a 2% aqueous hydrochloric acid. The solution was concentrated to dryness under reduced pressure and the resulting residue was recrystallized from ethanol to obtain 7.5 g of white amorphous 5-piperidinoacetyl-8-hydroxycarbostyril (II) hydrochloride 1/2 hydrate having a melting point of 239° - 241° C. (with decomposition).

Workup

  1. customto react
  2. temperaturewhile heating
  3. temperatureunder refluxing
  4. filtrationThe reaction mixture was filtered
  5. customto recover the reaction product which
  6. washwas then washed with benzene
  7. dissolutionThe resulting insoluble material was dissolved in 150 ml of a 2% aqueous hydrochloric acid
  8. concentrationThe solution was concentrated to dryness under reduced pressure
  9. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-57f8e8aebf624c8e98f3a11b1d50c355
Source dataset
uspto-grants-1977_05
Patent number
US04022776

Reaction notes

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