Dimethylformamide → HCID 12899546, compound

HRID 569963Notes

Reaction equation

HRID 569963 reaction equation
Cl[CH2:2][CH:3]([OH:17])[CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][C:12](=[O:16])[NH:13]2)=[CH:8][CH:7]=1.[C:18]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C)C=O>C(Cl)(Cl)Cl>[OH:17][CH:3]([CH2:2][N:27]1[CH2:28][CH2:29][N:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:25][CH2:26]1)[CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][C:12](=[O:16])[NH:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70961-PhenylpiperazineHCID 21243013HCID 21243013, compound

Product 1

HCID 12899546HCID 12899546, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.1 Grams of 7-(3-chloro-2-hydroxypropoxy)-3,4-dihydrocarbostyril and 8 g of 4-phenylpiperazine are mixed with 50 ml of dimethylformamide and reacted at 50°-60° C. for 5 hours under stirring conditions. The reaction mixture is concentrated under a reduced pressure to dryness and the residue thus obtained is dissolved in 80 ml of chloroform, then the chloroform layer is washed 3 times with 5% of sodium hydrogencarbonate aqueous solution and washed 3 times with water and dried with anhydrous sodium sulfate. Chloroform is removed by distillation under a reduced pressure and the residue thus obtained is purified by a silica gel-chromatography [silica gel: Wako C-200, extracting solvent:chloroform:methanol=30:1 (v/v)]. Then the extracted product is converted into its hydrochloride by using ethanol containing hydrogen chloride and ethanol is removed by distillation under a reduced pressure. The thus obtained residue is recrystallized from water to obtain 5.6 g of 7-[2-hydroxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril.monohydrochloride.1/2 hydrate in the form of colorless crystals with a melting point of 122° C. (decomp.).

Workup

  1. customreacted at 50°-60° C. for 5 hours under stirring conditions
  2. concentrationThe reaction mixture is concentrated under a reduced pressure to dryness
  3. customthe residue thus obtained
  4. washthe chloroform layer is washed 3 times with 5% of sodium hydrogencarbonate aqueous solution
  5. washwashed 3 times with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customChloroform is removed by distillation under a reduced pressure
  8. customthe residue thus obtained
  9. customis purified by a silica gel-chromatography [silica gel: Wako C-200, extracting solvent:chloroform:methanol=30:1 (v/v)]
  10. additioncontaining hydrogen chloride and ethanol
  11. customis removed by distillation under a reduced pressure
  12. customThe thus obtained residue is recrystallized from water

Sources & evidence

ORD record
ord-feba0b4fad4c4f9394527d247c0f5daf
Source dataset
uspto-grants-1988_03
Patent number
US04734416

Reaction notes

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