Toluene → 2-Methyl-1-[4-piperazinophenyl]-2-morpholino propan-1-one

HRID 1433108Notes

Reaction equation

HRID 1433108 reaction equation
[CH3:1][C:2]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)=[O:4].[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C1(C)C=CC=CC=1>ClCCl.[Cu]I>[CH3:1][C:2]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 1140TolueneHCID 4837PiperazineHCID 154053051-(4-Fluorphenyl)-2-methyl-2-morpholino-1-propanone

Product 1

HCID 579346002-Methyl-1-[4-piperazinophenyl]-2-morpholino propan-1-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent

Procedure

4.2 g of 2-methyl-1-[4-fluorophenyl]-2-morpholinopropan-1-one (0.0167 moles), 5.75 g of piperazine (0.0669 moles), 0.063 g of copper (I) iodide and 15 ml of toluene were mixed in a three necked flask equipped with a stirrer, nitrogen inlet, condenser, nitrogen outlet and a temperature probe. The mixture was heated to reflux for a total of 24 hours under a constant flow of nitrogen gas. The mixture was then cooled to room temperature, after which it was dissolved in 75 ml of dichloromethane. The mixture was then extracted with 100 ml of a saturated aqueous sodium chloride solution and then with 2×100 ml of water. The dichloromethane layer was then dried using anhydrous magnesium sulphate. The magnesium sulphate was removed by filtration and the organic solvent was then removed on a rotary evaporator to yield the product.

Workup

  1. customequipped with a stirrer, nitrogen inlet, condenser, nitrogen outlet
  2. temperatureThe mixture was heated
  3. temperatureto reflux for a total of 24 hours under a constant flow of nitrogen gas
  4. extractionThe mixture was then extracted with 100 ml of a saturated aqueous sodium chloride solution
  5. dry with materialThe dichloromethane layer was then dried
  6. customThe magnesium sulphate was removed by filtration
  7. customthe organic solvent was then removed on a rotary evaporator
  8. customto yield the product

Sources & evidence

ORD record
ord-6b148dcc6da6414096c7c73de7ba7538
Source dataset
uspto-grants-2009_11
Patent number
US07612122B2

Reaction notes

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