Bromoacetonitrile → {[3-(2-Benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amino}-acetonitrile

HRID 2219209Notes

Reaction equation

HRID 2219209 reaction equation
Br[CH2:2][C:3]#[N:4].[CH2:5]([C:12]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][NH:18][CH:19]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>O1CCOCC1.CCOC(C)=O>[CH2:5]([C:12]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:2][C:3]#[N:4])[CH:19]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:28]1[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 69273773[3-(2-Benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amine

Product 1

HCID 86610927{[3-(2-Benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amino}-acetonitrileYield 97%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Bromoacetonitrile (0.575 mL, 8.25 mmol) is added to a stirred solution of [3-(2-benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amine (2.76 g, 5.50 mmol) and diisopropylethylamine (1.44 mL, 8.25 mmol) in anhydrous 1,4-dioxane (20 mL) at ambient temperature under nitrogen. The mixture is heated at 90° C. for 4 hours. At ambient temperature, EtOAc (100 mL) and half-saturated aqueous NaHCO3 solution (100 mL) are added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica (gradient 5-16% EtOAc in hexane) to give 2.88 g (5.32 mmol, 97% yield) of the title compound as oil. ESIMS: m/z 541 [(M+H)+, 35Cl], 543 [(M+H)+, 37Cl]. Analysis for C33H33ClN2O3: calcd: C, 73.25; H, 6.15; N, 5.18; found: C, 73.05; H, 6.28; N, 5.02.

Workup

  1. customThe organic layer is separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is chromatographed on silica (gradient 5-16% EtOAc in hexane)

Sources & evidence

ORD record
ord-f0e370598f674621b5ecf4675b96246c
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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