Benzene → 5-Piperidinoacetyl-8-hydroxycarbostyril

HRID 1283410Notes

Reaction equation

HRID 1283410 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:17])[NH:10]2)=[O:4].[CH:18]([NH2:22])([CH2:20][CH3:21])C.[CH:23]1C=CC=C[CH:24]=1>>[N:22]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:17])[NH:10]3)=[O:4])[CH2:18][CH2:20][CH2:21][CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 241BenzeneHCID 24874Sec-ButylamineHCID 135332315-Chloroacetyl-8-methoxy-3,4-dihydrocarbostyril

Product 1

HCID 131952785-Piperidinoacetyl-8-hydroxycarbostyril

Procedure

10 g of 5-chloroacetyl-8-hydroxycarbostyril (IV) 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 (IIb) hydrochloride 1/2 hydrate having a melting point of 239° to 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-db8a65b45df3427cb120dc2ff2200157
Source dataset
uspto-grants-1976_08
Patent number
US03975391

Reaction notes

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