Piperazine → HCID 22721070, compound

HRID 1582479Notes

Reaction equation

HRID 1582479 reaction equation
[C:1](Cl)(Cl)=[O:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[NH:15][C:14]([C:24]3[CH:29]=[CH:28][C:27]([N:30]([CH3:32])[CH3:31])=[CH:26][C:25]=3[O:33][CH2:34][CH3:35])=[N:13]2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[NH:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>C1COCC1.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[CH:16]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:15]([C:1]([N:43]3[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]3)=[O:2])[C:14]([C:24]3[CH:29]=[CH:28][C:27]([N:30]([CH3:31])[CH3:32])=[CH:26][C:25]=3[O:33][CH2:34][CH3:35])=[N:13]2)=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 4837PiperazineHCID 6371PhosgeneHCID 8471TriethylamineHCID 10151602HCID 10151602, compound

Product 1

HCID 22721070HCID 22721070, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Phosgene (0.47 mL, 0.91 mmol, 1.93 M in toluene) was added to a stirred solution of {4-[4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-3-ethoxy-phenyl}-dimethyl-amine (83 mg, 0.18 mmol) and triethylamine (0.14 mL, 1 mmol) in THF (3 mL) at 0° C. over a period of 5 min. The mixture was stirred for 1 h and evaporated. The residue was dissolved in methylene chloride (2 mL) and added dropwise to a stirred solution of piperazine (0.239 g, 2.77 mmol) in methylene chloride (2 mL) at room temperature for 1 h. The mixture was diluted with aqueous sodium bicarbonate and extracted with methylene chloride. The organic extracts were washed with brine and dried over sodium sulfate. Evaporation of the solvents and chromatography of the residue over silica gel using 0-10% methanol in methylene chloride gave [4,5-bis-(4-chloro-phenyl)-2-(4-dimethylamino-2-ethoxy-phenyl)-4,5-dihydro-imidazol-1-yl]-piperazin-1-yl-methanone as a white foam (68 mg, 66%). HR-MS (ES, m/z) calculated for C30H34N5O2Cl2[(M+H)+]566.2084, observed 566.2088.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in methylene chloride (2 mL)
  3. extractionextracted with methylene chloride
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvents and chromatography of the residue over silica gel using 0-10% methanol in methylene chloride

Sources & evidence

ORD record
ord-7e622b7a2b7a45329a0d57bf3324c141
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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