Sodium Carbonate → 6-(1-Piperazinyl)-3,4-dihydrocarbostyril hydrobromide

HRID 1649207Notes

Reaction equation

HRID 1649207 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.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:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]3)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 12692731Ethanamine, 2-bromo-N-(2-bromoethyl)-, hydrobromide (1:1)

Product 1

HCID 132363086-(1-Piperazinyl)-3,4-dihydrocarbostyril hydrobromideYield 50.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9.36 g of 6-amino-3,4-dihydrocarbostyril, 18 g of bis(β-bromoethyl)amine monohydrobromide and 70 ml of methanol was refluxed for 15 hours while stirring. After cooling, 3.06 g of sodium carbonate was added and the resulting mixture was refluxed for 8 hours while stirring. The reaction mixture was cooled to precipitate crystals which then were collected by filtration, the crystals were washed with methanol to give 9.1 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril hydrobromide, m.p. 289°-293° C. (decomp.) (methanol-water), colorless needles.

Workup

  1. temperaturewas refluxed for 15 hours
  2. temperatureAfter cooling
  3. temperaturethe resulting mixture was refluxed for 8 hours
  4. stirringwhile stirring
  5. temperatureThe reaction mixture was cooled
  6. customto precipitate crystals which
  7. filtrationthen were collected by filtration
  8. washthe crystals were washed with methanol

Sources & evidence

ORD record
ord-3ee0b5548b504582ae82015b3d0a310e
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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