Sodium Iodide → 6-{4-[4-(2-Chloro-6-methlphenyl)-1-piperazinyl]-1-butenyl}-3,4-dihydrocarbostyril

HRID 2291192Notes

Reaction equation

HRID 2291192 reaction equation
Cl[CH2:2][CH2:3][CH:4]=[CH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2.[I-].[Na+].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:21]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[OH-].[Na+]>CN(C)C=O.CCOCC.C(N(CC)CC)C>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:21]=1[N:27]1[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH:4]=[CH:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]3)[CH2:31][CH2:32]1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 146249951-(2-Chloro-6-methylphenyl)piperazineHCID 544375796-(4-Chloro-1-butenyl)-3,4-dihydrocarbostyril

Product 1

HCID 540924146-{4-[4-(2-Chloro-6-methlphenyl)-1-piperazinyl]-1-butenyl}-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

2.8 Grams of 6-(4-chloro-1-butenyl)-3,4-dihydrocarbostyril and 2.1 g of sodium iodide were dissolved in 40 ml of dimethylformamide and stirred at 50° C. for 1 hour. To this solution were added 2.7 g of 4-(2-chloro-6-methylphenyl)piperazine and 1.5 g of triethylamine and the mixture was further stirred at 50° C. for 5 hours. The reaction mixture was concentrated under a reduced pressure to dryness to obtain a residue. To the residue were added 10N-NaOH and ether and stirred at a room temperature for 30 minutes to precipitate crystals. The crystals were separated by a silica-gel chromatography and recrystallized from ethanol-acetone-chloroform to obtain 6-{4-[4-(2-chloro-6-methylphenyl)-1-piperazinyl]-1-butenyl}-3,4-dihydrocarbostyril in colorless prism-like crystals. Yield: 2.7 g. Melting point: 179°-180° C.

Workup

  1. stirringthe mixture was further stirred at 50° C. for 5 hours
  2. concentrationThe reaction mixture was concentrated under a reduced pressure to dryness
  3. customto obtain a residue
  4. stirringstirred at a room temperature for 30 minutes
  5. customto precipitate crystals
  6. customThe crystals were separated by a silica-gel chromatography
  7. customrecrystallized from ethanol-acetone-chloroform

Sources & evidence

ORD record
ord-c8eba11caf46408789576d714decac5f
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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