Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[O:7][N:6]=1.[F:15][C:16]([F:30])([F:29])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:1].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:26]3[CH2:25][CH2:24][N:23]([C:19]4[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:29])([F:30])[F:15])[CH:18]=4)[CH2:28][CH2:27]3)=[N:6][O:7][C:8]=2[CH:13]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 6.5 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 5.8 g of N-(α,α,α-trifluoro-m-tolyl)piperazine, 7.0 g of potassium carbonate and a few crystals potassium iodide in 80 ml of dimethylformamide was stirred at 70°-75° C. for seven hrs. The reaction mixture was cooled, filtered and concentrated to an oil, which was stirred with water and extracted with ether-ethyl acetate. The organic extracts were washed with water (2×), saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated to an oil, which was converted to a salt by treatment with ethereal hydrogen chloride. The salt was recrystallized from ethyl acetate/methanol to give 4 g (35%) of product mp, 208°-209° C.
Workup
- temperatureThe reaction mixture was cooled
- filtrationfiltered
- concentrationconcentrated to an oil, which
- extractionextracted with ether-ethyl acetate
- washThe organic extracts were washed with water (2×), saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe mixture was filtered
- concentrationconcentrated to an oil, which
- customThe salt was recrystallized from ethyl acetate/methanol
Sources & evidence
- ORD record
- ord-c2676640fd80454395df9609f6d257ce
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04610988
Linked notes
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