Water → HCID 12899470, compound
Reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([OH:13])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4].[H-].[Na+].CN(C)[CH:18]=[O:19].Cl[CH2:22][CH:23]([OH:37])[CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:27][CH2:26]1.[OH2:38]>>[C:18]([OH:19])(=[O:37])[C:3]([OH:4])=[O:38].[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([O:13][CH2:22][CH:23]([OH:37])[CH2:24][N:25]3[CH2:30][CH2:29][N:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:27][CH2:26]3)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4]Participants
Procedure
1.8 Grams of 1-methyl-5-hydroxy-3,4-dihydrocarbostyril and 1 g of NaH (50% in oil) are mixed with 30 ml of dimethylformamide. Then 2.6 g of 1-chloro-2-hydroxy-3-(4-phenylpiperazinyl)propane are added thereto at a room temperature and stirred at 70° to 80° C. for 3 hours. The reaction mixture is poured into water and the organic layer is extracted with chloroform. After removing chloroform by distillation, the thus obtained residue is dissolved in acetone and the pH of the solution is adjusted by adding an acetone solution of oxalic acid. The crystals precipitated are collected by filtration and recrystallized from methanol-acetone to obtain 2.8 g of 1-methyl-5-[2-hydroxy-3-(4-phenylpiperazinyl)-propoxy]-3,4-dihydrocarbostyril oxalate in the form of colorless crystals with a melting point of 220°-221° C. (decomp.).
Workup
- extractionthe organic layer is extracted with chloroform
- customAfter removing chloroform
- distillationby distillation
- dissolutionthe thus obtained residue is dissolved in acetone
- additionby adding an acetone solution of oxalic acid
- customThe crystals precipitated
- filtrationare collected by filtration
- customrecrystallized from methanol-acetone
Sources & evidence
- ORD record
- ord-7c76f1092db94eaeb2e5ac567a26ddb6
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04734416
Reaction notes
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