Sodium Iodide → 3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]-propoxy}-4-methyl-benzoic acid hydrochloride salt

HRID 229096Notes

Reaction equation

HRID 229096 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[Na+].[I-].[C:8]([O-:11])([O-])=[O:9].[K+].[K+].[C:14]1([CH:20]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:21][NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[C:25]=2[Cl:34])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[ClH:34].[Cl:34][C:25]1[C:26]([C:30]([F:31])([F:32])[F:33])=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:22]([CH2:21][CH:20]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:2][CH2:3][CH2:4][O:5][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][C:14]=1[CH3:20])[C:8]([OH:11])=[O:9]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 58913799(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amine

Product 1

HCID 688622453-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]-propoxy}-4-methyl-benzoic acid hydrochloride saltYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a stirring solution of 3-bromo-propanol (77 ul, 0.84 mmol) in acetonitrile (10 ml) was added NaI (0.25 g, 1.7 mmol) and K2CO3 (0.23 g, 1.7 mmol). The mixture was stirred at 85° C. for 1 h, and then N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethyl-benzyl)amine (0.43 g, 1.12 mmol) was added. The reaction mixture was heated at 85° C. overnight. Solvent was removed, the residue was washed with H2O, and extracted twice with EtOAc. The EtOAc extracts were dried over Na2SO4, filtered, and concentrated. The crude mixture was purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm) to give 225 mg (60%) of the title compound as a white solid. MS (ESI) 448.0 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated at 85° C. overnight
  2. customSolvent was removed
  3. washthe residue was washed with H2O
  4. extractionextracted twice with EtOAc
  5. dry with materialThe EtOAc extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude mixture was purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm)

Sources & evidence

ORD record
ord-cc2d5cb395af49998c0631ffefbec38e
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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