Diethyl Ether → HCID 53739889, compound

HRID 2291190Notes

Reaction equation

HRID 2291190 reaction equation
O[CH:2]([C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:30])[CH2:24][CH2:23]2)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=2[CH3:19])[CH2:8][CH2:7]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+].C(OCC)C>ClC(Cl)C>[CH3:19][C:13]1[C:14]([CH3:18])=[CH:15][CH:16]=[CH:17][C:12]=1[N:9]1[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][CH:3]=[CH:2][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[NH:26][C:25](=[O:30])[CH2:24][CH2:23]3)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 20229430HCID 20229430, compound

Product 1

HCID 53739889HCID 53739889, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2.8 Grams of 6-{1-hydroxy-4-[4-(2,3-dimethylphenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril and 0.5 g of p-toluenesulfonic acid were dissolved in 100 ml of dichloroethane then the mixture was refluxed for 20 minutes. The reaction mixture was concentrated under a reduced pressure to dryness then to the residue thus obtained were added 10N-NaOH and diethyl ether and stirred at a room temperature for 30 minutes. The crystals thus precipitated were collected by filtration and separated by a silica-gel chromatography. Recrystallized from ethanol-acetone-chloroform to obtain 6-{4-[4-(2,3-dimethylphenyl)piperazinyl]-1-butenyl}-3,4-dihydrocarbostyril in colorless needle-like crystals. Yield: 1.9 g.

Workup

  1. temperaturethe mixture was refluxed for 20 minutes
  2. concentrationThe reaction mixture was concentrated under a reduced pressure to dryness
  3. customto the residue thus obtained
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration
  6. customseparated by a silica-gel chromatography
  7. customRecrystallized from ethanol-acetone-chloroform

Sources & evidence

ORD record
ord-bdd6caf7b9824d6da07a6d41651b3443
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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