Sodium Carbonate → HCID 13236375, compound

HRID 1649257Notes

Reaction equation

HRID 1649257 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.Br.[Br:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[BrH:14].[N:1]1([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[NH:10][C:9](=[O:12])[CH:8]=[CH:7]3)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12692731Ethanamine, 2-bromo-N-(2-bromoethyl)-, hydrobromide (1:1)HCID 133171128-Aminoquinolin-2(1H)-one

Product 1

HCID 13236375HCID 13236375, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Aminocarbostyril (15.47 g, 96.6 mmols) and bis(β-bromoethyl)amine hydrobromide (33 g, 106 mmols) were suspended in DMF and the suspension was stirred at 70° to 80° C. for 10 hours. After adding 5.1 g of sodium carbonate the reaction mixture was stirred at the same temperature as above for 7 hours. After distilling off the solvent under reduced pressure, methanol was added to the residue to crystallize. The crude crystals thus obtained were recrystallized from methanol-ether to give 5.1 g of 8-(1-piperazinyl)carbostyril hydrobromide, m.p. above 300° C., colorless scales.

Workup

  1. stirringwas stirred at the same temperature as above for 7 hours
  2. distillationAfter distilling off the solvent under reduced pressure, methanol
  3. additionwas added to the residue
  4. customto crystallize
  5. customThe crude crystals thus obtained
  6. customwere recrystallized from methanol-ether

Sources & evidence

ORD record
ord-f59ee3fb5da545a8bae2259602b057d7
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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