Phenyl (3,4-dimethylisoxazol-5-yl)carbamate → N-(3,4-dimethylisoxazol-5-yl)-4-[3-(4-fluorophenoxy)benzylidene]piperidine-1-carboxamide

HRID 1666353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666353
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.[CH3:23][C:24]1[C:28]([CH3:29])=[C:27]([NH:30][C:31](=O)[O:32]C2C=CC=CC=2)[O:26][N:25]=1>>[CH3:23][C:24]1[C:28]([CH3:29])=[C:27]([NH:30][C:31]([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:32])[O:26][N:25]=1

Komponenten

3

Edukt 2

HCID 53485970Phenyl (3,4-dimethylisoxazol-5-yl)carbamateHCID 668760974-[3-(4-Fluoro-phenoxy)-benzylidene]-piperidine hydrochloride

Produkt 1

HCID 24968687N-(3,4-dimethylisoxazol-5-yl)-4-[3-(4-fluorophenoxy)benzylidene]piperidine-1-carboxamideAusbeute 116,3 %

Versuchsvorschrift

Following the procedure in Example 1, Step 6, 4-[3-(4-fluoro-phenoxy)-benzylidene]-piperidine hydrochloride (200 mg, 0.625 mmol, from Example 18, Step 3) and phenyl 3,4-dimethylisoxazol-5-ylcarbamate (160 mg, 0.40 mmol) were used to provide the title compound (196 mg). MS (APCI 10 V) AP+ 422.2, 284.2, AP− 420.2; 1H NMR (400 MHz, CD3OD) δ ppm 1.83 (s, 3H) 2.18 (s, 3H) 2.42 (td, J=5.76, 1.10 Hz, 2H) 2.51 (td, J=5.88, 1.13 Hz, 2H) 3.47-3.52 (m, 2H) 3.57-3.63 (m, 2H) 6.40 (s, 1H) 6.77-6.84 (m, 2H) 6.94-6.98 (m, J=7.78, 1.45, 0.77, 0.77 Hz, 1H) 6.98-7.03 (m, 2H) 7.05-7.13 (m, 2H) 7.29 (t, J=7.85 Hz, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-e48a2c9cbe424b2aa39217e215a23bda
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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