2,6-Dimethylmorpholine → HCID 14553929, compound

HRID 1904286Notes

Reaction equation

HRID 1904286 reaction equation
[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:19]2[C:20]([CH2:30]C(C)C)=[C:21](C)C=CC=2S([O-])(=O)=O)[CH:16]=[CH:17][CH:18]=1>[OH-].[Na+]>[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH2:19][CH:20]([CH3:30])[CH2:21][N:4]2[CH2:5][CH:6]([CH3:8])[O:7][CH:2]([CH3:1])[CH2:3]2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 1108622,6-DimethylmorpholineHCID 86743101HCID 86743101, compound

Product 1

HCID 14553929HCID 14553929, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2,6-Dimethylmorpholine (10.0 g) was heated to 100° C. with stirring, and 3-(m-methoxymethoxyphenyl)-2-methylpropyl-p-toluenesulfonate (5.0 g) was dropwise added thereto in 1 hour. The reaction mixture was aged at 100° C. for 2 hours with stirring, cooled to room temperature, and after addition of 15% aqueous sodium hydroxide (50 ml), extracted with diethyl ether (50 ml×3). The organic layer was combined, washed with a saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to give 4-[3-(m-methoxymethoxyphenyl)-2-methylpropyl]-2,6-dimethylmorpholine (1.2 g).

Workup

  1. waitThe reaction mixture was aged at 100° C. for 2 hours
  2. stirringwith stirring
  3. extractionextracted with diethyl ether (50 ml×3)
  4. washwashed with a saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b92a7c0054284d4880e95c8651ccb6af
Source dataset
uspto-grants-1989_06
Patent number
US04837236

Reaction notes

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