Sodium Carbonate → HCID 20480595, compound

HRID 1649254Notes

Reaction equation

HRID 1649254 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.Br.[Br:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[Na+].[Na+]>CO>[BrH:14].[N:1]1([C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]3)=[CH:4][CH:3]=2)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 52002427-amino-3,4-dihydro-1H-quinolin-2-oneHCID 12692731Ethanamine, 2-bromo-N-(2-bromoethyl)-, hydrobromide (1:1)

Product 1

HCID 20480595HCID 20480595, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 23 g of 7-amino-3,4-dihydrocarbostyril, 48 g of bis(β-bromoethyl)amine hydrobromide and 200 ml of methanol was refluxed with stirring for 8 hours. After cooling to room temperature, 7.52 g of sodium carbonate was added to the mixture followed by refluxing while stirring for additional 8 hours. After distilling off methanol under reduced pressure, isopropanol was added to the residue. After cooling, crystals which precipitated were collected by filtration and recrystallized from ethanol 3 times to give 15 g of 7-(1-piperazinyl)-3,4-dihydrocarbostyril hydrobromide, m.p. 174°-177° C., colorless granules.

Workup

  1. temperaturewas refluxed
  2. temperatureby refluxing
  3. stirringwhile stirring for additional 8 hours
  4. distillationAfter distilling off methanol under reduced pressure, isopropanol
  5. additionwas added to the residue
  6. temperatureAfter cooling
  7. customcrystals which precipitated
  8. filtrationwere collected by filtration
  9. customrecrystallized from ethanol 3 times

Sources & evidence

ORD record
ord-e1c583d879be4953828065ad81a70d6b
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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