4-Nitrobenzaldehyde → 4-(Azetidin-1-yl-methyl)-nitrobenzene

HRID 24928

Reaktionsgleichung

Reaktionsgleichung von HRID 24928
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH:13]1[CH2:16][CH2:15][CH2:14]1.C([BH3-])#N.[Na+]>C(O)C.C(OCC)(=O)C>[N:13]1([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:16][CH2:15][CH2:14]1

Komponenten

6

Edukt 3

HCID 5414-NitrobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 12308726Azetidine hydrochloride

Produkt 1

HCID 225696534-(Azetidin-1-yl-methyl)-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6.2 g (41 mmol) of 4-nitrobenzaldehyde and 3.8 g (40.6 mmol) of azetidine-hydrochloride are dissolved in 120 ml of ethanol. 2.6 g (41 mmol) of sodium cyanoborohydride are added at 0° C. The mixture is slowly heated to ambient temperature and then stirred for 18 hours. Then the solvent is eliminated in vacuo, the residue is taken up in ethyl acetate and washed with water. The solvent is eliminated in vacuo and after chromatography of the residue on silica gel (ethyl acetate/methanol/NH4OH=95:5:0.5) a light brown oil is obtained.

Aufarbeitung

  1. washwashed with water
  2. customafter chromatography of the residue on silica gel (ethyl acetate/methanol/NH4OH=95:5:0.5) a light brown oil is obtained

Quellen und Nachweise

ORD-Eintrag
ord-ebebe92616344816b517ea4dc75ba6dd
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855710B2

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