Potassium Carbonate → HCID 22185398, compound

HRID 2105301Notes

Reaction equation

HRID 2105301 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[O:12][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 767382-Methoxy-4-nitrophenolHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 22185398HCID 22185398, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-methoxy-4-nitro-phenol Compound 36a (0.92 g, 5.4 mmol), potassium carbonate (1.5 g, 10.8 mmol) and 4-(2-chloro-ethyl)-morpholine hydrochloride Compound 56a (1.04 g, 5.65 mmol) in DMF (10 mL) was heated under microwave conditions to 140° C. for 30 minutes. The reaction mixture was filtered, diluted with EtOAc and subsequently washed with water, then brine. The organic layer was dried over sodium sulfate and concentrated to yield 4-[2-(2-methoxy-4-nitro-phenoxy)-ethyl]-morpholine Compound 56b (1.46 g). 1H NMR (400 MHz, CDCl3) δ 7.90 (dd, 1H); 7.77 (d, 1H); 6.93 (d, 1H); 4.26 (t, 2H); 3.97 (s, 3H); 3.79-3.69 (m, 4H); 2.91 (t, 2H); 2.66-2.55 (m, 4H). MS 283 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with EtOAc
  3. washsubsequently washed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2b2d4981b77e43f98530e352531fb2c0
Source dataset
uspto-grants-2009_08
Patent number
US07579356B2

Reaction notes

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