Sodium hydride → 2-[(1-Methyl-4-piperidinyl)oxy]-5-nitropyridine
Reaktionsgleichung
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=1.[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1>C1COCC1>[CH3:20][N:17]1[CH2:18][CH2:19][CH:14]([O:13][C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=2)[CH2:15][CH2:16]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
557 mg of NaH (14 mmol) suspended in 10 ml of THF are placed under nitrogen. The mixture is cooled to 0° C. and a solution of 1.5 g (9.3 mmol) of 2-chloro-5-nitropyridine and 1.28 g (11.1 mmol) of 4-hydroxy-1-methylpiperidine in 15 ml of THF is added dropwise. The reaction mixture is refluxed for 4 hours. After hydrolysing the excess NaH, the solvent is evaporated off under reduced pressure. The residue is taken up in ethyl acetate and washed with water and then with saturated NaCl solution. It is then dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0 v/v) up to 100/4 v/v) to give 1.1 g of 2-(1-methylpiperidin-4-yloxy)-5-nitropyridine.
Aufarbeitung
- temperatureThe reaction mixture is refluxed for 4 hours
- customthe solvent is evaporated off under reduced pressure
- washwashed with water
- dry with materialIt is then dried over Na2SO4
- filtrationfiltered
- customthe filtrate is evaporated under reduced pressure
- customThe residue is chromatographed on silica gel
- washeluting with a DCM/MeOH mixture from (100/0 v/v) up to 100/4 v/v)
Quellen und Nachweise
- ORD-Eintrag
- ord-4d9e1ae15a884949b0e7493e37eef7ff
- Quelldatensatz
- uspto-grants-2015_09
- Patentnummer
- US09120812B2
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