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

HRID 734824

反応式

HRID 734824 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c3c43faa4ea44b69a685af769a8c04d0
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

関連ノート

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