Methanol → HCID 21243038, compound

HRID 621557Notes

Reaction equation

HRID 621557 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][N:5]1[C:15]2[C:10](=[C:11]([O:16][CH2:17][CH:18]3[O:20][CH2:19]3)[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:6]1=[O:7].[C:22]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CO.[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38]>CC(C)=O>[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][N:5]1[C:15]2[C:10](=[C:11]([O:16][CH2:17][CH:18]([OH:20])[CH2:19][N:31]3[CH2:32][CH2:33][N:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:29][CH2:30]3)[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:6]1=[O:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 971Oxalic AcidHCID 70961-PhenylpiperazineHCID 14517402HCID 14517402, compound

Product 1

HCID 21243038HCID 21243038, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2.9 grams of 1-(3-methylbutyl)-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril and 1.7 g of 4-phenylpiperazine are mixed with 50 ml of methanol and reacted at 50°-60° C. for 3 hours. The reaction mixture is concentrated under reduced pressure and the residue thus obtained is dissolved in 50 ml of acetone. Into this solution, 20 ml of an acetone solution containing 1.1 g of oxalic acid are added, then the precipitate thus formed is collected by filtration, washed with acetone and dried. Recrystallization from ethanol-ether to obtain 2.1 g of 1-(3-methylbutyl)-5-[2-hydroxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril monooxalate in the form of colorless crystals. This product is confirmed as a single compound by a silica-gel thin layer chromatography-(developing solvent; chloroform:methanol=9:1).

Workup

  1. customreacted at 50°-60° C. for 3 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customthe residue thus obtained
  4. additionare added
  5. customthe precipitate thus formed
  6. filtrationis collected by filtration
  7. washwashed with acetone
  8. customdried
  9. customRecrystallization from ethanol-ether

Sources & evidence

ORD record
ord-ed12293d4a284ccc891dc5cbd712ce79
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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