Tetrahydrofuran → N-[4-methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenyl)-acetamide

HRID 1012164Notes

Reaction equation

HRID 1012164 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8]O)[CH2:4][CH2:3]1.[H-].[Na+].F[C:13]1[C:14]([O:26][CH3:27])=[CH:15][C:16]([N+:23]([O-:25])=[O:24])=[C:17]([NH:19][C:20](=[O:22])[CH3:21])[CH:18]=1.C1C[O:31]CC1>>[CH3:27][O:26][C:14]1[C:13]([O:31][CH2:1][N:2]2[CH2:3][CH2:4][CH:5]([CH3:8])[CH2:6][CH2:7]2)=[CH:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[C:16]([N+:23]([O-:25])=[O:24])[CH:15]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 2719711-Methyl-4-piperidinemethanolHCID 604094N-(5-Fluoro-4-methoxy-2-nitrophenyl)acetamide

Product 1

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

Procedure

To a solution of 1-methyl-4-piperidinemethanol (0.566 g, 4.3 mmol) in THF (25 ml) at 0° C. was added, portion wise, 60% NaH (0.63 g, 15.48 mmol) and the mixture stirred for 15 mins. N-(5-Fluoro-4-methoxy-2-nitro-phenyl)-acetamide [U.S. Pat. No. 4,431,807] (1 g, 4.38 mmol) in THF (40 ml) was added to reaction, which was stirred at RT for 30 mins followed by heating at 50° C. for 1 hour. The reaction was quenched with water and then extracted with EtOAc twice, the organic portion was washed with brine, dried over MgSO4, filtered and reduced in vacuo to yield N-[4-methoxy-5-(4-methyl-piperidin-1-ylmethoxy)-2-nitro-phenyl]-acetamide (1.34 g), (LC/MS (acidic method): Rt 1.84, [M+H]+ 338)

Workup

  1. temperatureby heating at 50° C. for 1 hour
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc twice
  4. washthe organic portion was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f57893867b2042839dbeaaea46944118
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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