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

HRID 857912Notes

Reaction equation

HRID 857912 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.O.C(OCC)(=O)C>O1CCCC1>[N:14]1([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)=[O:4])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8857Ethyl AcetateHCID 668402-Bromo-4'-nitroacetophenone

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2-bromo-4′-nitroacetophenone (4.0 g) in dry tetrahydrofuran (60 mL) was treated with morpholine (2.84 mL). After stirring at room temperature for a further 30 minutes the reaction mixture was treated with water (100 mL) and ethyl acetate (100 mL). The organic phase was separated, washed with brine (100 mL), then dried over magnesium sulfate and evaporated. The residue was triturated with diethyl ether to give the title compound (2.72 g) as a yellow solid, Rf 0.60 (dichloromethane:methanol:triethylamine, 85:10:5). 1H NMR [(CD3)2SO]: δ 8.32 (d, 2H), 8.20 (d, 2H), 3.90 (s, 2H), 3.58 (t, 4H) and 2.48 (t, 4H).

Workup

  1. customThe organic phase was separated
  2. washwashed with brine (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-19e5631b41554f82b951f35d75a8ca30
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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