Potassium Iodide → HCID 57253530, compound

HRID 584241Notes

Reaction equation

HRID 584241 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17]Cl)[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=1)=[O:7].Cl.[CH2:38]([O:40][C:41]([C@@H:43]1[CH2:48][O:47][CH2:46][CH2:45][NH:44]1)=[O:42])[CH3:39].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][N:44]2[CH2:45][CH2:46][O:47][CH2:48][C@H:43]2[C:41]([O:40][CH2:38][CH3:39])=[O:42])[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=1)=[O:7]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 44828818Ethyl (3S)-morpholine-3-carboxylate--hydrogen chloride (1/1)HCID 53806279HCID 53806279, compound

Product 1

HCID 57253530HCID 57253530, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-chloro-2-butynyl]piperazine (1.2 g) and (3S)-3-ethoxycarbonylmorpholine hydrochloride (0.43 g), potassium carbonate (1.09 g) and a trace of potassium iodide in N,N-dimethylformamide (50 ml) was stirred at 55° C. for 12 hours. After cooling, the solvent was removed by evaporation, and ethyl acetate and water were added thereto. The organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (2:3) as an eluent to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-((3S)-3-ethoxycarbonylmorpholino)-2-butynyl]piperazine (0.29 g) as an oil.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by evaporation, and ethyl acetate and water
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (2:3) as an eluent

Sources & evidence

ORD record
ord-4a822fcec353451ba420705534a97aea
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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