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

HRID 1757408Notes

Reaction equation

HRID 1757408 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 retool) and trifluoroacetic acid (0.57 g, 5.0 retool) in dichloromethane (55 mL). The resulting solution was stirred at room temperature for an additional 10 to15 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 ofthe 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 apale yellow oil. 1H-NMR (300 MHz, CDCl3): δ=1.80-1.92 (1H,m), 2.43-2.55 (1H, m), 2.63-2.75 (2H, m), 2.88-2.96 (2H, m), 3.71 (2H, AB quartet, JAB =13.0 Hz), 3.78-3.86 (1H, m), 7.25-7.41 (6H, m), 7.53-7.66 (3H, m).

Workup

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

Sources & evidence

ORD record
ord-3f2de50141b74c4d81f4169e08061f52
Source dataset
uspto-grants-1995_08
Patent number
US05446044

Reaction notes

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