Acetonitrile → 1-Benzylpyrrolidine-3-carbonitrile

HRID 16244

Reaction equation

HRID 16244 reaction equation
CS(O[CH:6]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1)(=O)=O.C(=O)(O)[O-].[Na+].[C:23](#[N:25])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:11]([N:8]1[CH2:9][CH2:10][CH:6]([C:23]#[N:25])[CH2:7]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 98998111-Benzylpyrrolidin-3-yl methanesulfonate

Product 1

HCID 46745791-Benzylpyrrolidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Procedure

A mixture of EXAMPLE 1G (1.5 g) and tetrabutlyammonium cyanide (3.15 gm) in acetonitrile (25 mL) was heated at 65° C. for 24 hours, poured into saturated aqueous sodium bicarbonate, and extracted with toluene. The extract was washed with distilled water, dried over anhydrous sodium sulfate, and concentrated. 1H NMR (300 MHz, CDCl3) δ 7.33 (s, 5H), 3.42 (m, 2H), 2.89 (m, 1H), 2.72 (m, 1H), 1.68 (b, 3H), 1.45 (m, 2H).

Workup

  1. extractionextracted with toluene
  2. washThe extract was washed with distilled water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0f73c1e849cc445a98e72179d7bd2338
Source dataset
uspto-grants-2010_06
Patent number
US07737159B2

Linked notes

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