Morpholine → N-(2-methoxy-6-nitrophenyl)-2-morpholin-4-ylacetamide

HRID 1095384

Reaction equation

HRID 1095384 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:15][CH3:16])=[O:4].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C1COCC1>[CH3:16][O:15][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 574360272-bromo-N-(2-methoxy-6-nitrophenyl)acetamide

Product 1

HCID 57436028N-(2-methoxy-6-nitrophenyl)-2-morpholin-4-ylacetamideYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-N-(2-methoxy-6-nitrophenyl)acetamide (Step 1, 8.8 g, 30 mmol) in THF (240 mL) was added morpholin (11 mL, 122 mmol) at 0° C. and warmed to rt. After 2.5 h, the reaction mixture was quenched by addition of water (200 mL) and extracted with ethyl acetate (200 mL×2). The combined organic layers were washed with water (200 mL), brine (100 mL) dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1) to afford 6.7 g (75%) of the title compound.

Workup

  1. customthe reaction mixture was quenched by addition of water (200 mL)
  2. extractionextracted with ethyl acetate (200 mL×2)
  3. washThe combined organic layers were washed with water (200 mL), brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-184fbfc0ca2f49c98231e4027798ca7a
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Linked notes

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