Benzaldehyde → HCID 11735591, compound

HRID 645479Notes

Reaction equation

HRID 645479 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])(O)(=O)=O.[Na+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[C-:20]#[N:21].[Na+]>O.C([O-])(O)=O.[Na+]>[C:2]1([CH:1]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:20]#[N:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 8929Sodium CyanideHCID 31268PyrrolidineHCID 516919Sodium Bisulfate

Product 1

HCID 11735591HCID 11735591, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of benzaldehyde (9.4 mmol) in H2O (6 mL) are added sodium hydrogensulfate (9.4 mmol) and pyrrolidine (9.4 mmol). After stirring at room temperature for 0.5 h, to the suspension is added sodium cyanide (9.4 mmol), and the resulting mixture is stirred at room temperature for 15 h. The reaction mixture is diluted with sat. aq. NaHCO3, then extracted with AcOEt. The organic extracts are washed with water (×2) and brine, dried over Na2SO4, filtered, and concentrated in vacuo to give phenylpyrrolidin-1-ylacetonitrile, which is directly used for the next reaction without further purification.

Workup

  1. stirringthe resulting mixture is stirred at room temperature for 15 h
  2. extractionextracted with AcOEt
  3. washThe organic extracts are washed with water (×2) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cadd43009c11484496a70cae8eab2e7b
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

Loading…