Morpholine → HCID 29801728, compound

HRID 1042672Notes

Reaction equation

HRID 1042672 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-cdfc5a65c17a4d16a2669e46d1084f4a
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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