Triethylamine → 2-Nitro-5-[4-(1-piperidyl)-1-piperidyl]pyridine

HRID 72780

Reaktionsgleichung

Reaktionsgleichung von HRID 72780
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH2:12]1.C(N(CC)CC)C>CS(C)=O>[N+:8]([C:5]1[CH:4]=[CH:3][C:2]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][N:6]=1)([O-:10])=[O:9]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 786071,4'-BipiperidineHCID 8176205-Bromo-2-nitropyridine

Produkt 1

HCID 675134152-Nitro-5-[4-(1-piperidyl)-1-piperidyl]pyridineAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To 5-bromo-2-nitropyridine (1.2 g, 5.9 mmol) in DMSO (4 mL) was added 1-(4-piperidyl)piperidine (1.0 g, 5.9 mmole) and triethyl amine (0.99 mL, 7.1 mmole). The contents were heated to 120 degrees in a CEM Discovery microwave system for 3 hours. The crude reaction was then loaded over a silica gel column and eluted with DCM/methanol (0-20%) to afford 2-nitro-5-[4-(1-piperidyl)-1-piperidyl]pyridine as an oil (457 mg). 1H NMR (600 MHz, DMSO-d6) δ ppm 1.26-1.36 (m, 2H) 1.43 (m, 6H) 1.76 (m, 2H) 2.37 (m, 5H) 2.94 (t, J=12.74 Hz, 2H) 4.06 (d, J=13.47 Hz, 2H) 7.41 (dd, J=9.37, 2.64 Hz, 1H) 8.08 (d, J=9.37 Hz, 1H) 8.20 (d, J=2.64 Hz, 1H).

Aufarbeitung

  1. temperatureThe contents were heated to 120 degrees in a CEM Discovery microwave system for 3 hours
  2. customThe crude reaction
  3. washeluted with DCM/methanol (0-20%)

Quellen und Nachweise

ORD-Eintrag
ord-46ba32e6ce7b49a9b8c44128e132509e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829012B2

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