Phenethylamine → 1-[4-(2-Phenethylaminoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

HRID 723335Notes

Reaction equation

HRID 723335 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[C:12]2=[O:29])=[CH:7][CH:6]=1.[CH2:30]([NH2:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH2:30]([NH:38][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[C:12]2=[O:29])=[CH:7][CH:6]=1)[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 120958581-[4-(2-Bromoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

Product 1

HCID 120958591-[4-(2-Phenethylaminoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[4-(2-bromoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one (50 mg) in acetonitrile (1 ml) was mixed with phenethylamine (47 mg), potassium carbonate (70 mg) and sodium iodide (5 mg) and boiled under reflux for 2 hours. The cooled solution was filtered and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 491.60 (C31 H29N3O3); MS (ESI): 492 ([M+H]+), was obtained as hydroformate in this way.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationThe cooled solution was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC
  5. customMS (ESI): 492 ([M+H]+), was obtained as hydroformate in this way

Sources & evidence

ORD record
ord-18078aaea69c4964b1bc75fcbff2a532
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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