Sodium Iodide → 3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}-bromobenzene

HRID 902605Notes

Reaction equation

HRID 902605 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Na+].[I-].Br[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([Br:20])[CH:17]=[CH:18][CH:19]=1.[Cl:21][C:22]1[C:43]([C:44]([F:47])([F:46])[F:45])=[CH:42][CH:41]=[CH:40][C:23]=1[CH2:24][NH:25][CH2:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(#N)C>[Cl:21][C:22]1[C:43]([C:44]([F:45])([F:46])[F:47])=[CH:42][CH:41]=[CH:40][C:23]=1[CH2:24][N:25]([CH2:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([Br:20])[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 19389133HCID 19389133, compoundHCID 58913799(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amine

Product 1

HCID 597014793-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}-bromobenzeneYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (140 mg, 1.0 mmol) and NaI (82 mg, 0.34 mmol) were added to a solution of 3-(3-bromopropoxy)bromobenzene (100 mg, 0.34 mmol), (2-chloro-3-trifluoromethylbenzyl)(2,2-diphenylethyl)amine and acetonitrile (3 mL). The mixture was heated at reflux for 16 h. The mixture was allowed to cool to RT and concentrated in vacuo. The residue was partitioned between methylene chloride and 10% NaHCO3 aq. solution and layers separated. The aqueous layer was extracted with methylene chloride (2×10 mL). The organic layers were combined, dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: 0.1% trifluoroacetic acid in acetonitrile B: 0.1% aqueous trifluoroacetic acid, A: 10 to 90% during 10 min, UV detection at 254 nm) to give 52 mg (29%) of the title compound as an oil. MS (ESI) 639.2 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between methylene chloride and 10% NaHCO3 aq. solution and layers
  5. customseparated
  6. extractionThe aqueous layer was extracted with methylene chloride (2×10 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min

Sources & evidence

ORD record
ord-7362dbaca0634b06b3cdb8300b47732a
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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