Morpholine → 2-(Morpholin-4-yl)-1-(4-nitrophenyl)ethan-1-one

HRID 2105299Notes

Reaction equation

HRID 2105299 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:10].CCN(C(C)C)C(C)C>C1COCC1>[N:1]1([CH2:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[O:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 668402-Bromo-4'-nitroacetophenoneHCID 81531Diisopropylethylamine

Product 1

HCID 2297452-(Morpholin-4-yl)-1-(4-nitrophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Morpholine Compound 50b (1.41 mL, 16.2 mmol) was added dropwise to a solution of 2-bromo-1-(4-nitro-phenyl)-ethanone Compound 50a (4.15 g, 16.2 mmol) in THF (50 mL) and DIPEA (3.1 mL, 17.8 mmol). The reaction was stirred for 3 hours and then extracted from 0.5 M NaH2PO4 with EtOAc. The combined extracts were dried over MgSO4, filtered and evaporated down. The residue was recrystallized from EtOAc and hexanes to give 2-morpholin-4-yl-1-(4-nitro-phenyl)-ethanone Compound 50c (2.55 g) as a yellow solid. MS 251 (MH+).

Workup

  1. extractionextracted from 0.5 M NaH2PO4 with EtOAc
  2. dry with materialThe combined extracts were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated down
  5. customThe residue was recrystallized from EtOAc and hexanes

Sources & evidence

ORD record
ord-9b8784482727428cbeb58736c08e1b7f
Source dataset
uspto-grants-2009_08
Patent number
US07579356B2

Reaction notes

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