Ethylene Glycol → (4-Bromo-2-methylphenyl)-[2-(4-methylpiperidin-1-yl)ethyl]amine

HRID 734824

반응식

HRID 734824 반응식
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][NH2:10])[CH2:4][CH2:3]1.[Br:11][C:12]1[CH:17]=[CH:16][C:15](I)=[C:14]([CH3:19])[CH:13]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)(C)C.[Cu]I>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:10][CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]2)=[C:14]([CH3:19])[CH:13]=1

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 7837002-(4-Methylpiperidin-1-yl)ethan-1-amineHCID 27246015-Bromo-2-iodotoluene

생성물 1

HCID 69054033(4-Bromo-2-methylphenyl)-[2-(4-methylpiperidin-1-yl)ethyl]amine

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3776Isopropanol용매

실험 절차

5.00 g (35.00 mmol) of 2-(4-methylpiperidin-1-yl)ethylamine was added under argon to a mixture of 10.39 g (35.00 mmol) of 4-bromo-1-iodo-2-methylbenzene, 0.33 g (1.75 mmol) of CuI, 30.0 g (141.00 mmol) of potassium phosphate, and 4.34 g (70.00 mmol) of ethylene glycol in 35 mL of isopropanol and the mixture was refluxed for 15 hours. The reaction mixture was evaporated down in vacuo and the residue taken up in EtOAc. The organic phase was washed with 5% aqueous ammonia, dried over magnesium sulfate, and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, EtOAc). Yield: 1.20 g (11% of theoretical); C15H23BrN2 (M=311.261); calc.: molpeak (M+H)+: 311/313 (Br); found: molpeak (M+H)+: 311/313 (Br); HPLC-MS: 4.24 minutes (method B).

후처리

  1. temperaturethe mixture was refluxed for 15 hours
  2. customThe reaction mixture was evaporated down in vacuo
  3. washThe organic phase was washed with 5% aqueous ammonia
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down in vacuo
  6. customThe crude product was purified by column chromatography (silica gel, EtOAc)
  7. custom4.24 minutes (method B)

출처 및 근거

ORD 기록
ord-c3c43faa4ea44b69a685af769a8c04d0
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592358B2

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