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

HRID 227848

반응식

HRID 227848 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cd927df962af4339be37943796b0e34d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560582B2

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