Hydrochloric Acid → HCID 12899466, compound

HRID 621573Notes

Reaction equation

HRID 621573 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH:15]([OH:23])[CH2:16][N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32].C([O-])(O)=O.[Na+].[ClH:38]>C(O)C.CN(C)C=O.C(N(CC)CC)C>[ClH:38].[ClH:38].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH:15]([OH:23])[CH2:16][N:17]2[CH2:18][CH2:19][N:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])[CH2:21][CH2:22]2)=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 113582-BromoanisoleHCID 516892Sodium BicarbonateHCID 14128501HCID 14128501, compound

Product 1

HCID 12899466HCID 12899466, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2.5 grams of 8-bromo-5-(2-hydroxy-3-piperazinylpropoxy)-3,4-dihydrocarbostyril, 2.0 g of o-bromoanisole and 2.0 g of triethylamine are mixed with 30 ml of dimethylformamide. The reaction mixture thus obtained is heated under a stream of argon gas at 120° to 130° C. for 5 hours. The reaction mixture is concentrated under a reduced pressure and to the residue thus obtained is added 30 ml of 5% NaHCO3 aqueous solution, and the organic layer is extracted with chloroform. Chloroform is removed by distillation and to the residue thus obtained are added 3 ml of concentrated hydrochloric acid, then 20 ml of ethanol are added and stirred. The crystals thus precipitated are collected by filtration to obtain 2.1 g of 8-bromo-5-{2-hydroxy-3-[4-(2-methoxyphenyl)piperazinyl]-propoxy}-3,4-dihydrocarbostyril.dihydrochloride in the form of colorless crystals with a melting point of 226°-228° C.

Workup

  1. customThe reaction mixture thus obtained
  2. temperatureis heated under a stream of argon gas at 120° to 130° C. for 5 hours
  3. concentrationThe reaction mixture is concentrated under a reduced pressure and to the residue
  4. customthus obtained
  5. extractionthe organic layer is extracted with chloroform
  6. customChloroform is removed by distillation and to the residue
  7. customthus obtained
  8. customThe crystals thus precipitated
  9. filtrationare collected by filtration

Sources & evidence

ORD record
ord-5bcb0a9b2554498784ca761156e3b31f
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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