Diisopropylethylamine → Benzo[d]isoxazol-3-yl(4-(4-chlorophenoxy)piperidin-1-yl)methanone
Reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:26]([C:33](Cl)=[O:34])=[N:25]1>ClCCl.C(OCC)(=O)C>[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:26]([C:33]([N:10]2[CH2:9][CH2:8][CH:7]([O:6][C:5]3[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:12][CH2:11]2)=[O:34])=[N:25]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-(4-chlorophenoxy)piperidine (26 mg, 0.12 mmol), and N,N-diisopropylethylamine (0.086 mL, 0.49 mmol) in dichloromethane (0.5 mL) was added dropwise a solution of benzo[d]isoxazole-3-carbonyl chloride (22 mg, 0.12 mmol) in dichloromethane (0.5 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate (3 mL) and washed with water (1.5 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) and then preparative LC-MS to give 16.3 mg (37% yield) of the title compound.
Workup
- washwashed with water (1.5 mL)
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate)
Sources & evidence
- ORD record
- ord-36bcb924382c4a8db4d73e601405ff10
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051296B2
Reaction notes
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