Ethyl Acetate → 3-(4-(Oxetan-3-yl)piperazin-1-yl)pyridin-4-amine

HRID 1850684Notes

Reaction equation

HRID 1850684 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:20][O:19][CH2:18]2)[CH2:13][CH2:12]1)([O-])=O.CCOC(C)=O>CO.[Ni]>[O:19]1[CH2:20][CH:17]([N:14]2[CH2:13][CH2:12][N:11]([C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[NH2:1])[CH2:16][CH2:15]2)[CH2:18]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 904113171-(4-Nitro-1-oxido-pyridin-1-ium-3-yl)-4-(oxetan-3-yl)piperazine

Product 1

HCID 904131553-(4-(Oxetan-3-yl)piperazin-1-yl)pyridin-4-amineYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-(4-nitro-1-oxido-pyridin-1-ium-3-yl)-4-(oxetan-3-yl)piperazine (553 mg, 1.973 mmol) in MeOH (15 mL)/EtOAc (25 mL) was passed through the H-cube apparatus to hydrogenate over raney nickel at 20° C. and full H2 mode, flow rate 1 ml/min. The solvent was removed in vacuo to give the title compound 7l as an orange solid (462 mg, 100% Yield).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c3482af00b8c4e61b0112b13aef72baa
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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