Potassium Iodide → 1-[3,5-Bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-4-[3-(3-pyridyl)-2-propynyl]piperazine

HRID 1374991Notes

Reaction equation

HRID 1374991 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[CH:16]=1)=[O:7].Cl.Cl[CH2:40][C:41]#[C:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:40][C:41]#[C:42][C:43]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)[CH2:10][CH:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[CH:16]=1)=[O:7]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 179639311-[3,5-Bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]piperazineHCID 694194203-(3-Pyridyl)-2-propynyl chloride hydrochloride

Product 1

HCID 210769821-[3,5-Bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-4-[3-(3-pyridyl)-2-propynyl]piperazineYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-[3,5-bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]piperazine (0.4 g), 1-chloro-3-(3-pyridyl)-2-propyne hydrochloride (0.17 g), potassium carbonate (0.52 g) and a trace of potassium iodide in N,N-dimethylformamide (7 ml) was stirred for 4 hours at 80° C. After cooling, the solvent was removed by evaporation, and ethyl acetate and aqueous sodium hydrogen carbonate solution were added thereto. The organic layer was separated, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate. The fractions containing the objective compound were collected and evaporated under reduced pressure to give 1-[3,5-bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-4-[3-(3-pyridyl)-2-propynyl]piperazine (0.44 g) as an oil.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by evaporation, and ethyl acetate and aqueous sodium hydrogen carbonate solution
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. additionThe fractions containing the objective compound
  9. customwere collected
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a343710e88bd47988fb4ca32ca0842a1
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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