Morpholine → N-(2,5-Dimethylphenyl)morpholine

HRID 227848

Reaction equation

HRID 227848 reaction equation
CC([O-])(C)C.[Na+].Br[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[CH3:15].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[CH3:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 23676156Sodium t-butoxide

Product 1

HCID 11052463N-(2,5-Dimethylphenyl)morpholineYield 95.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

An oven-dried resealable Schlenk tube was purged with argon and charged with Pd2(dba)3 (13.9 mg, 0.015 mmol, 3.0 mol % Pd), 2 [Example 1] (17.9 mg, 0.045 mmol, 4.5 mol %), and NaOt-Bu (140 mg, 1.4 mmol). The tube was purged with argon, fitted with a rubber septum and then DME (0.5 mL), 2-bromo-p-xylene (140 μL, 1.01 mmol) and morpholine (105 μL, 1.2 mmol) were added via syringe. The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at room temperature for 24 h. The reaction mixture was then diluted with ether (20 mL), filtered through celite and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 185 mg (95%) of a colorless oil.

Workup

  1. customAn oven-dried resealable Schlenk tube was purged with argon
  2. customThe tube was purged with argon
  3. customfitted with a rubber septum
  4. customThe septum was removed
  5. customthe tube was sealed with a teflon
  6. customscrew cap
  7. additionThe reaction mixture was then diluted with ether (20 mL)
  8. filtrationfiltered through celite and
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-cd927df962af4339be37943796b0e34d
Source dataset
uspto-grants-2009_07
Patent number
US07560582B2

Linked notes

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