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

HRID 734824

Reaction equation

HRID 734824 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c3c43faa4ea44b69a685af769a8c04d0
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Linked notes

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