Potassium Carbonate → Methyl 2-[2-(morpholin-4-ylmethyl)-5-ethylphenoxy]propanoate

HRID 369448Notes

Reaction equation

HRID 369448 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][C:9]=2[OH:16])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][C:9]=2[O:16][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 232864162-(Morpholin-4-ylmethyl)-5-ethylphenol

Product 1

HCID 15483901Methyl 2-[2-(morpholin-4-ylmethyl)-5-ethylphenoxy]propanoateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a 250 mL round bottom flask equipped with a mechanical stirrer and a thermometer was added 5.0 grams (0.0.023 mole--1.0 equiv.) of 2-(morpholin-4-ylmethyl)-5-ethylphenol, 4.54 grams (0.027 mole--1.2 equiv.) of methyl 2-bromopropanoate, 3.75 grams (0.027 mole--1.2 equiv.) of potassium carbonate, and 50 mL (%Wt/Vol. Phenol to Solvent--10%) of methylethylketone. The reaction mixture was heated to reflux where it stirred for 27 hours. After this period, the reaction mixture was analyzed by GC, which indicated the reaction was complete. The reaction mixture was filtered and washed with diethylether. The filtrate was concentrated under reduced pressure, yielding 7.0 grams of 96% pure methyl 2-[2-(morpholin4-ylmethyl)-5-ethylphenoxy]propanoate (95.2% yield).

Workup

  1. customTo a 250 mL round bottom flask equipped with a mechanical stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux where it
  4. waitAfter this period
  5. filtrationThe reaction mixture was filtered
  6. washwashed with diethylether
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-51b999a88c1343f3a60f9bdd7f73ca44
Source dataset
uspto-grants-2000_10
Patent number
US06136972

Reaction notes

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