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

HRID 54466Notes

Reaction equation

HRID 54466 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, hexanesethyl 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, hexanesethyl acetate 5:1)

Sources & evidence

ORD record
ord-35e798838f264c45b7381865c9caea92
Source dataset
uspto-grants-1997_04
Patent number
US05622966

Reaction notes

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