Phenyl benzo[c]isoxazol-3-ylcarbamate → N-2,1-benzisoxazol-3-yl-4-[3-(4-fluorophenoxy)benzylidene]piperidine-1-carboxamide
Reaction equation
Cl.[F:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=2)[CH:11]=[C:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1.[N:23]1[O:24][C:25]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)=[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=12>>[N:23]1[O:24][C:25]([NH:32][C:33]([N:15]2[CH2:14][CH2:13][C:12](=[CH:11][C:10]3[CH:18]=[CH:19][CH:20]=[C:8]([O:7][C:6]4[CH:5]=[CH:4][C:3]([F:2])=[CH:22][CH:21]=4)[CH:9]=3)[CH2:17][CH2:16]2)=[O:34])=[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=12Participants
3
Procedure
Following the procedure in Example 1, Step 6, 4-[3-(4-fluoro-phenoxy)-benzylidene]-piperidine hydrochloride (200 mg, 0.625 mmol) (Step 3) and phenyl benzo[c]isoxazol-3-ylcarbamate (175 mg, 0.688 mmol) were used to provide the title compound (275 mg). MS (APCI 10V) AP+ 444.2, 284.2, AP− 442.2; 1H NMR (400 MHz, CDCl3) δ ppm 2.46-2.52 (m, 2H) 2.57-2.63 (m, 2H) 3.56-3.62 (m, 2H) 3.66-3.72 (m, 2H) 6.39 (s, 1H) 6.78-6.87 (m, 2H) 6.91-6.96 (m, J=7.93, 1.25, 0.68, 0.57 Hz, 1H) 6.97-7.07 (m, 4H) 7.25-7.31 (m, 2H) 7.47 (dt, J=8.41, 0.77 Hz, 1H) 7.50-7.55 (m, 1H) 7.71 (s, 1H) 8.09 (d, J=7.90 Hz, 1H).
Sources & evidence
- ORD record
- ord-fe701d7233434af9a9f64fb8283397d4
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08044052B2
Reaction notes
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