Sodium hydride → 1-Benzyl-5-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril

HRID 621571Notes

Reaction equation

HRID 621571 reaction equation
[CH2:1]([N:8]1[C:18]2[C:13](=[C:14]([OH:19])[CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28][CH2:27]1>CN(C)C=O>[CH2:1]([N:8]1[C:18]2[C:13](=[C:14]([O:19][CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:28][CH2:27]3)[CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139197Piperazine, 1-(3-chloropropyl)-4-phenyl-HCID 140106821-benzyl-5-hydroxy-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 128995481-Benzyl-5-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyrilYield 46.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 grams of 1-benzyl-5-hydroxy-3,4-dihydrocarbostyril and 0.48 g of 50% oily NaH are mixed with 30 ml of dimethyl formamide and stirred, then 4 g of 1-chloro-3-(4-phenylpiperazinyl)propane are added therein and warmed to 50°-60° C. for 2.5 hours. The reaction mixture is concentrated under a reduced pressure and the residue thus obtained is extracted with chloroform. After removing the chloroform by distillation, the thus obtained residue is recrystallized from ligroin to obtain 2.1 g of 1-benzyl-5-[3-(4-phenylpiperazinyl)-propoxy]-3,4-dihydrocarbostyril in the form of pale yellowish needle-like crystals with a melting point of 113° C.

Workup

  1. temperaturewarmed to 50°-60° C. for 2.5 hours
  2. concentrationThe reaction mixture is concentrated under a reduced pressure
  3. customthe residue thus obtained
  4. extractionis extracted with chloroform
  5. customAfter removing the chloroform
  6. distillationby distillation
  7. customthe thus obtained residue is recrystallized from ligroin

Sources & evidence

ORD record
ord-4bcf2a8dbacd4dfcb19ce098c647c23e
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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