Hydrazine hydrate (1:1) → 3-Benzyl-3-azabicyclo(3.1.0)hexan-6-amine

HRID 712482Notes

Reaction equation

HRID 712482 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[N+:14]([O-])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.O>[Ni].CO>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[NH2:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 215851823-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane

Product 1

HCID 185069973-Benzyl-3-azabicyclo(3.1.0)hexan-6-amineYield 104.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 3-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane (4.00 g) and a catalytic amount of Raney nickel in MeOH was added slowly a solution of 98% H2NNH2—H2O (70 mL) at rt. The mixture was stirred for 5 h at room temperature and filtered. The filtrate was concentrated in vacuo to give the title compound as brown oil (3.60 g) and the crude product was used for the next step without further purification. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 204.3 (M+1).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a3338bfb92f0451ca9e679207868fa8a
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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