1-(4-Nitrophenyl)azetidine → Benzenamine,4-(1-azetidinyl)-

HRID 594814Notes

Reaction equation

HRID 594814 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[N:10]1([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 5917181-(4-Nitrophenyl)azetidine

Product 1

HCID 45078992Benzenamine,4-(1-azetidinyl)-Yield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (70 mg) was added to a solution of 1-(4-nitrophenyl)azetidine (0.7 g, 3.9 mmol) in EtOH (15 mL) at r.t. under N2. After stirring under 50 psi H2 overnight, the reaction mixture was filtered through Celite and concentrated to give 580 mg (99%) of the title compound as a brown oil. [M+H] Calc'd for C9H12N2, 149. Found, 149.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1fb2d44776e144a893e9528fd2c78119
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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