Methyl iodide → 4-(3-Methoxyphenyl)morpholine

HRID 349695

Reaction equation

HRID 349695 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:14]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.CCOCC>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1413433-Morpholinophenol

Product 1

HCID 99643354-(3-Methoxyphenyl)morpholine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 3-morpholinyl-phenol (3.8 g; 21.2 mmol) and powdered K2CO3 (4.4 g; 31.8 mmol) in dry DMF (15 mL) was added iodomethane (1.45 mL; 23.3 mmol) via syringe at room temperature under nitrogen atmosphere. The resulting mixture was allowed to stir at room temperature for 22 hours. The reaction was diluted with ether (150 mL) and washed successively with water (2×40 mL) and brine (40 mL), then dried (MgSO4), filtered and concentrated in vacuo to provide the desired ether as a yellow oil (2.51 g; 61%).

Workup

  1. washwashed successively with water (2×40 mL) and brine (40 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide the desired ether as a yellow oil (2.51 g; 61%)

Sources & evidence

ORD record
ord-5888eead817d4f8ab60508cb457f9058
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Linked notes

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