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

HRID 1795633ノート

反応式

HRID 1795633 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-446c326b917145228528b4edbb7f2442
出典データセット
uspto-grants-2006_04
特許番号
US07026498B2

反応ノート

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