Hydrochloric Acid → 6-(3-(4-(2-Methoxyphenyl)-1-piperazinyl)-1-piperazinyl)-1-propenyl-3,4-dihydrocarbostyril

HRID 1462548Notes

Reaction equation

HRID 1462548 reaction equation
O[CH:2]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]2)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[CH2:7][CH2:6]1.Cl.[OH-].[Na+]>O1CCOCC1>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH:3]=[CH:2][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]3)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13064856HCID 13064856, compound

Product 1

HCID 30670946-(3-(4-(2-Methoxyphenyl)-1-piperazinyl)-1-piperazinyl)-1-propenyl-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.8 Grams of 6- {-1-hydroxy-3-[4-(2-methoxy- phenyl)-1-piperazinyl]propyl}-3,4-dihydrocarbostyril was dissolved in 100 ml of dioxane and 5 ml of concentrated hydrochloric acid was added thereto, then the mixture was refluxed for 15 minutes. The reaction mixture was concentrated under a reduced pressure to dryness to obtain a residue. To the residue were added 10N-NaOH and further and stirred at a room temperature for 30 minutes to precipitate crystals. The crystals were collected by filtration, washed with ether then recrystallized from ethanol- chloroform-acetone to obtain 6-{3-[4-(2-methoxyphenyl)- 1-piperazinyl]-1-propenyl}-3,4-dihydrocarbostyril in colorless needle-like crylstals. Yield: 2.3 g. Melting point: 174°-175° C.

Workup

  1. temperaturethe mixture was refluxed for 15 minutes
  2. concentrationThe reaction mixture was concentrated under a reduced pressure to dryness
  3. customto obtain a residue
  4. customto precipitate crystals
  5. filtrationThe crystals were collected by filtration
  6. washwashed with ether
  7. customthen recrystallized from ethanol- chloroform-acetone

Sources & evidence

ORD record
ord-d906b3afd6044bf7aaf1fd843a17ac20
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

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