4-Methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenylamine → 4-Methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-benzene-1,2-diamine

HRID 1012166Notes

Reaction equation

HRID 1012166 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:7][C:6]([NH2:18])=[C:5]([N+:19]([O-])=O)[CH:4]=1>[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:19])[C:6]([NH2:18])=[CH:7][C:8]=1[O:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([CH3:17])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 671063144-Methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenylamine

Product 1

HCID 671062864-Methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-benzene-1,2-diamineYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-Methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenylamine (0.9 g, 3.0 mmol) and 10% palladium on carbon (90 mg) in MeOH (20 ml) was shaken under an atmosphere of hydrogen for 4 hours. The reaction mixture was filtered through GF/A paper directly into saturated EtOAc/HCl to give a purple solution, which was reduced in vacuo to yield 4-Methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-benzene-1,2-diamine as a purple foam (0.8 g), (LC/MS (acidic method): Rt 0.34, [M+H]+ 266)

Workup

  1. filtrationThe reaction mixture was filtered through GF/A paper directly into saturated EtOAc/HCl
  2. customto give a purple solution, which

Sources & evidence

ORD record
ord-bf8ba13e79b34255810013ccda093a57
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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