Potassium Carbonate → 3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

HRID 1296973Notes

Reaction equation

HRID 1296973 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.C([O-])([O-])=O.[K+].[K+].[C:28]1([CH:34]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:35][NH:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[C:39]=2[Cl:48])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(#N)C>[C:49]1([CH:34]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:35][N:36]([CH2:2][CH2:3][CH2:4][OH:5])[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:45])([F:46])[F:47])[C:39]=2[Cl:48])[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 1859152-NaphthylalanineHCID 58913799(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amine

Product 1

HCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-olYield 60%

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 Nal (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. The reaction mixture was concentrated, the residue was dissolved in EtOAc, and washed with H2O. 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. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with H2O
  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-42ed2d0e15fc41ea88872396f69aa001
Source dataset
uspto-grants-2007_07
Patent number
US07247748B2

Reaction notes

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