Phenyl pyridin-3-ylcarbamate → 4-[3-(4-fluorophenoxy)benzylidene]-N-pyridin-3-ylpiperidine-1-carboxamide

HRID 1666354Notes

Reaction equation

HRID 1666354 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[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30](=O)[O:31]C2C=CC=CC=2)[CH:24]=1>>[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=2)[CH:11]=[C:12]2[CH2:13][CH2:14][N:15]([C:30]([NH:29][C:25]3[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=3)=[O:31])[CH2:16][CH2:17]2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 6935890Phenyl pyridin-3-ylcarbamateHCID 668760974-[3-(4-Fluoro-phenoxy)-benzylidene]-piperidine hydrochloride

Product 1

HCID 249686884-[3-(4-fluorophenoxy)benzylidene]-N-pyridin-3-ylpiperidine-1-carboxamideYield 94.4%

Procedure

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 pyridin-3-ylcarbamate (147 mg, 0.688 mmol) were used to provide the title compound (238 mg). MS (APCI 10 V) AP+ 404.3, AP− 402.1; 1H NMR (400 MHz, CD3OD) δ ppm 2.43 (td, J=5.79, 1.10 Hz, 2H) 2.52 (td, J=5.89, 1.01 Hz, 2H) 3.51-3.55 (m, 2H) 3.60-3.66 (m, 2H) 6.40 (s, 1H) 6.78-6.84 (m, 2H) 6.95-6.98 (m, J=7.67, 1.53, 0.75, 0.75 Hz, 1H) 6.98-7.04 (m, 2H) 7.05-7.15 (m, 2H) 7.30 (t, J=7.77 Hz, 1H) 7.34 (ddd, J=8.41, 4.84, 0.76 Hz, 1H) 7.91 (ddd, J=8.38, 2.60, 1.45 Hz, 1H) 8.16 (dd, J=4.85, 1.46 Hz, 1H) 8.58 (dd, J=2.62, 0.67 Hz, 1H).

Sources & evidence

ORD record
ord-52a9c67b56bb4c74b3f0f50929bc249e
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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