Trifluoroacetic acid → 2-[1-(Phenylmethyl)-3-pyrrolidinyl]benzonitrile

HRID 1742843Notes

Reaction equation

HRID 1742843 reaction equation
[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[C:21]#[N:22])=[CH2:18].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[C:2]1([CH2:1][N:8]2[CH2:12][CH2:18][CH:17]([C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[C:21]#[N:22])[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 516892Sodium BicarbonateHCID 122378792-Ethenylbenzonitrile

Product 1

HCID 199590402-[1-(Phenylmethyl)-3-pyrrolidinyl]benzonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine (16.62 g, 70.0 mmol) in dichloromethane (15 mL) are added dropwise, over a 45-minute period, to a solution of 2-ethenylbenzonitrile (6.00 g, 46.0 mmol) and trifluoroacetic acid (0.57 g, 5.0 mmol) in dichloromethane (55 mL). The resulting solution was stirred at room temperature for an additional 10 to 15 minutes, and then heated with saturated aqueous sodium bicarbonate solution (ca 10-15 mL). The organic layer was decanted, washed with water, and dried over anhydrous magnesium sulfate. Filtration and concentration of the solution provided an orange oil which was chromatographed (silica-gel, hexanes-ethyl acetate 5:1) to afford the title compound (6.95 g, 58%) as a pale yellow oil.

Workup

  1. customThe organic layer was decanted
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationFiltration and concentration of the solution
  5. customprovided an orange oil which
  6. customwas chromatographed (silica-gel, hexanes-ethyl acetate 5:1)

Sources & evidence

ORD record
ord-ddb88362b06e4a13befdadd226a78e77
Source dataset
uspto-grants-1994_08
Patent number
US05342844

Reaction notes

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