Hydrogen Bromide → HCID 13324119, compound

HRID 1285424Notes

Reaction equation

HRID 1285424 reaction equation
CO[CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:13](=[O:28])[CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[NH:5][C:4]1=[O:29].Br.[OH2:31]>>[OH:31][C:7]1[CH:8]=[CH:9][C:10]([C:13](=[O:28])[CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:18][CH2:17]2)=[C:11]2[C:6]=1[NH:5][C:4](=[O:29])[CH2:3][CH2:12]2

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 131714511HCID 131714511, compound

Product 1

HCID 13324119HCID 13324119, compound

Procedure

To 19.7 g of methoxy-5-[1-oxo-3-(4-phenyl-1-piperazinyl)propyl]-3,4-dihydrocarbostyril was added 300 ml of 47%-hydrobromic acid and the mixture was refluxed for 18 hours. The reaction mixture was concentrated under a reduced pressure to dryness. Then to the residue thus obtained was added water and again concentrated under a reduced pressure to dryness. Acetone was added to the crystalline residue and collected by filtration and were recrystallize from methanol. The crystals were suspended in 500 ml of water and the suspension was neutralized with 5%-sodium hydroxide aqueous solution and crystalline precipitates thus formed were collected by filtration and were washed with water. 17.1 Grams of 8-hydroxy-5-[1-oxo-3-(4-phenyl-1-piperazinyl)propyl]-3,4-dihydrocarbostyril was obtained in amorphous-like crystals. Melting point: 287°-291° C.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. concentrationThe reaction mixture was concentrated under a reduced pressure to dryness
  3. customThen to the residue thus obtained
  4. concentrationagain concentrated under a reduced pressure to dryness
  5. additionAcetone was added to the crystalline residue
  6. filtrationcollected by filtration
  7. customwere recrystallize from methanol
  8. customcrystalline precipitates thus
  9. customformed
  10. filtrationwere collected by filtration
  11. washwere washed with water

Sources & evidence

ORD record
ord-112f5ada8eb848b793ad068b3169a451
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

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