Morpholine → HCID 29801728, compound

HRID 502718Notes

Reaction equation

HRID 502718 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH3:15])=[O:4].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:15][C:7]1[C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 46736583HCID 46736583, compound

Product 1

HCID 29801728HCID 29801728, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-N-(2-methyl-3-nitrophenyl)acetamide (0.5 g, 1.8 mmol) was dissolved in 15 ml of THF and to this was added morpholine (0.17 g, 2.0 mmol) and diisopropylethylamine (0.71 g, 5.5 mmol). The reaction was stirred at room temperature for 16 hours. The reaction was then partitioned between EtOAc and H2O. The aqueous mixture was extracted with EtOAc, and the combined organic layers were washed with H2O, brine and then dried over MgSO4. Solvent evaporation afforded N-(2-methyl-3-nitrophenyl)-2-morpholinoacetamide as a yellow solid.

Workup

  1. customThe reaction was then partitioned between EtOAc and H2O
  2. extractionThe aqueous mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with H2O, brine
  4. dry with materialdried over MgSO4
  5. customSolvent evaporation

Sources & evidence

ORD record
ord-94f9f5ed619746b68a7bdd91a9bd846f
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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