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

HRID 24928

Reaction equation

HRID 24928 reaction equation
[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

Participants

6

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 12308726Azetidine hydrochloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ebebe92616344816b517ea4dc75ba6dd
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Linked notes

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