Sodium Hydroxide → HCID 14553811, compound

HRID 1904279Notes

Reaction equation

HRID 1904279 reaction equation
[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.C1(C)C=CC(S(O[CH2:19][CH:20]([CH3:35])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:23]=2)(=O)=O)=CC=1.[OH-].[Na+]>O>[O:28]([C:24]1[CH:23]=[C:22]([CH2:21][CH:20]([CH3:35])[CH2:19][N:4]2[CH2:5][CH:6]([CH3:8])[O:7][CH:2]([CH3:1])[CH2:3]2)[CH:27]=[CH:26][CH:25]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1108622,6-DimethylmorpholineHCID 14553810HCID 14553810, compound

Product 1

HCID 14553811HCID 14553811, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,6-Dimethylmorpholine (1.16 g) was added to 3-(m-phenoxyphenyl)-2-methylpropyl p-toluenesulfonate (0.8 g) at room temperature, and the resultant mixture was stirred at 100° C. for 30 minutes. The reaction mixture was made basic with addition of water (100 ml) and 15% aqueous sodium hydroxide solution (10 ml) thereto and extracted with diethyl ether (50 ml×3). The ether 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-methylpropyl]-2,6-dimethylmorpholine (trans-isomer, 0.16 g; cis-isomer, 0.41 g).

Workup

  1. extractionextracted with diethyl ether (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-6c05163987cc4034a6331b66d7b809f0
Source dataset
uspto-grants-1989_06
Patent number
US04837236

Reaction notes

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