Propargyl bromide → HCID 13236341, compound

HRID 1649234Notes

Reaction equation

HRID 1649234 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH2:9][CH2:10][C:11](=[O:17])[NH:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:24](Br)[C:25]#[CH:26]>CN(C=O)C>[CH2:26]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH2:9][CH2:10][C:11](=[O:17])[NH:12]3)[CH2:2][CH2:3]1)[C:25]#[CH:24]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10340Sodium CarbonateHCID 11630008HCID 11630008, compound

Product 1

HCID 13236341HCID 13236341, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1 g of 5-(1-piperazinyl)-3,4-dihydrocarbostyril, 30 ml of DMF and 900 mg of sodium carbonate was added 491 mg of propargyl bromide and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was poured into a large amount of saturated saline solution and extracted with chloroform. After washing with water, the extract was dried over anhydrous sodium sulfate. Then, chloroform was distilled off and the residue was purified through silica gel column chromatography and recrystallized from chloroform to give 0.1 g of 5-[4-(2-propynyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 225°-226° C., pale yellow powders.

Workup

  1. additionThe reaction mixture was poured into a large amount of saturated saline solution
  2. extractionextracted with chloroform
  3. washAfter washing with water
  4. dry with materialthe extract was dried over anhydrous sodium sulfate
  5. distillationThen, chloroform was distilled off
  6. customthe residue was purified through silica gel column chromatography
  7. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-3e04f80dee2247808bc96698dbecf7a7
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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