1-(3-Methoxy-4-nitro-phenyl)-4-pyrrolidin-1-yl-piperidine → 2-Methoxy-4-(4-(pyrrolidin-1-yl)piperidin-1-yl)aniline

HRID 2222126Notes

Reaction equation

HRID 2222126 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.[H][H]>C1COCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

5

Reactant 2

HCID 574161471-(3-Methoxy-4-nitro-phenyl)-4-pyrrolidin-1-yl-piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 574161462-Methoxy-4-(4-(pyrrolidin-1-yl)piperidin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

321 mg (1.053 mmol) 1-(3-methoxy-4-nitro-phenyl)-4-pyrrolidin-1-yl-piperidine are dissolved in 10 ml THF, combined with 30 mg Raney nickel and then shaken for 9 days at 20° C. under 4 bar hydrogen atmosphere. The catalyst is filtered off and washed again with THF. The solvent is eliminated in vacuo.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed again with THF

Sources & evidence

ORD record
ord-839d56d415754bd09741174d660d841d
Source dataset
uspto-grants-2008_05
Patent number
US07371753B2

Reaction notes

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