1-(2-Methoxyphenyl)piperazine → HCID 18798273, compound

HRID 1003748Notes

Reaction equation

HRID 1003748 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19]Br)=[O:15])[C:12](=[O:21])[NH:11][C:10]=2[C:22]([O:24][CH3:25])=[O:23])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][N:37]3[CH2:36][CH2:35][N:34]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[O:27][CH3:26])[CH2:39][CH2:38]3)=[O:15])[C:12](=[O:21])[NH:11][C:10]=2[C:22]([O:24][CH3:25])=[O:23])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 18798275HCID 18798275, compound

Product 1

HCID 18798273HCID 18798273, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-(3,4-difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-1-(3-bromoprop-1-yl)aminocarbonyl-2(1H)-imidazolone (386 mg, 0.92 mmol), 4-(2-methoxyphenyl)piperazine (353 mg, 1.84 mmol), potassium carbonate (382 mg, 2.76 mmol) and sodium iodide (138 mg, 0.92 mmol) in dioxane (15 mL) was heated at reflux for 24 hours and then concentrated. The residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and concentrated to give the crude product which was flash chromatographed over silica gel eluting with EtOAc/MeOH (9:1) to give the desired product (2% yield). Hydrochloride salt: yellow solid; m.p. 122-124° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. concentrationconcentrated
  4. customThe residue was partitioned between EtOAc and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customchromatographed over silica gel eluting with EtOAc/MeOH (9:1)

Sources & evidence

ORD record
ord-1ff0baf4ca1b482b94328be23edaa93a
Source dataset
uspto-grants-2000_04
Patent number
US06046331

Reaction notes

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