Sodium Methoxide → 4-Methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenylamine

HRID 1012165Notes

Reaction equation

HRID 1012165 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]([NH:18]C(=O)C)=[C:5]([N+:22]([O-:24])=[O:23])[CH:4]=1.C[O-].[Na+]>CO>[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+:22]([O-:24])=[O:23])[CH:4]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67106627N-[4-methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenyl)-acetamide

Product 1

HCID 671063144-Methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenylamineYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[4-methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenyl]-acetamide (1.34 g, 3.97 mmol) in MeOH (40 ml) was added sodium methoxide (1 g, 18.5 mmol) reaction stirred RT for 48 hours then reduced in vacuo. The residue was triturated with water and the solid filtered and washed with further water. Solid dried to yield 4-Methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenylamine (0.9 g), (LC/MS (acidic method): Rt 1.72, [M+H]+ 296)

Workup

  1. customThe residue was triturated with water
  2. filtrationthe solid filtered
  3. washwashed with further water
  4. customSolid dried

Sources & evidence

ORD record
ord-074f69aa890e4c82a9feea1fdaeb35b8
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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