Acetonitrile → 1-Benzylpyrrolidine-3-carbonitrile

HRID 460437

Reaction equation

HRID 460437 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-ee0fd30836f540f28cd0f0bb79e4b6c3
Source dataset
uspto-grants-2007_03
Patent number
US07196200B2

Linked notes

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