2,6-Dimethylmorpholine → HCID 53873157, compound

HRID 1904284Notes

Reaction equation

HRID 1904284 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([CH3:18])[CH2:16]Br)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][CH:20]1[O:25][CH:24]([CH3:26])[CH2:23][NH:22][CH2:21]1>[OH-].[Na+]>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([CH3:18])[CH2:16][N:22]2[CH2:21][CH:20]([CH3:19])[O:25][CH:24]([CH3:26])[CH2:23]2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1108622,6-DimethylmorpholineHCID 54559692HCID 54559692, compound

Product 1

HCID 53873157HCID 53873157, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3-(m-Phenoxyphenyl)-2-methyl-2-propenyl bromide (1.0 g) was added to 2,6-dimethylmorpholine (2.0 g) at 0° C. while stirring, followed by aging at the same temperature for 3 hours. Ice water (100 ml) and 15% aqueous sodium hydroxide solution (30 ml) were added to the resultant mixture to make basic, followed by extraction with ethyl acetate (50 ml×3). The extracts were combined together, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to give 4-[3-(m-phenoxyphenyl)-2-methyl-2-propenyl]-2,6-dimethylmorpholine (cis-isomer, 0.3 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate (50 ml×3)
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6969805a84b24196952e531715b33db5
Source dataset
uspto-grants-1989_06
Patent number
US04837236

Reaction notes

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