Piperidine → 2-Chloro-4-(4-phenoxyphenyl)-6-(piperidin-1-yl)nicotinonitrile

HRID 81021

Reaktionsgleichung

Reaktionsgleichung von HRID 81021
[Cl:1][C:2]1[N:9]=C(Cl)C=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[C:3]=1[C:4]#[N:5].[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25].N1CCCC[CH2:32]1>C(#N)C>[Cl:1][C:2]1[N:9]=[C:24]([N:26]2[CH2:29][CH2:30][CH2:32][CH2:28][CH2:27]2)[CH:25]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 866656822,6-Dichloro-4-(4-phenoxyphenyl)nicotinonitrile

Produkt 1

HCID 866656832-Chloro-4-(4-phenoxyphenyl)-6-(piperidin-1-yl)nicotinonitrileAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A mixture of 2,6-dichloro-4-(4-phenoxyphenyl)nicotinonitrile (34 mg, 0.100 mmol, from Step 2 of Example 8), triethylamine (0.028 mL, 0.199 mmol), 0.5 M acetonitrile solution of piperidine (0.199 mL, 0.100 mmol) in acetonitrile (1 mL) was stirred at room temperature for 36 h to give a suspension. The white solid was collected by filtration, washed with cold methanol (1 mL), dried under vacuum to give 2-chloro-4-(4-phenoxyphenyl)-6-(piperidin-1-yl)nicotinonitrile (15 mg, 39% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.51 (2H, δ, J=8.53 Hz), 7.39 (2H, t, J=8.03 Hz), 7.18 (1H, t, J=7.40 Hz), 6.98-7.12 (4H, 6.45 (1H, s), 3.63-3.81 (4H, m), 1.62-1.90 (7H, m), 1.52-1.80 (6H, s), 1.58 (9H, s); MS (ES+) m/z: 390 (M+H); LC retention time: 4.293 min (analytical HPLC Method A).

Aufarbeitung

  1. customto give a suspension
  2. filtrationThe white solid was collected by filtration
  3. washwashed with cold methanol (1 mL)
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fb681d46cc434977b31aa084d4be3402
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846673B2

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