Acetone → 2-Methyl-2-(2-methyl-1-pyrrolidinyl)propanenitrile

HRID 20806

Reaction equation

HRID 20806 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.[CH3:7][C:8]([CH3:10])=O.[C-]#N.[K+].[N-:14]=[C:15]=O>O.C(Cl)Cl>[CH3:7][C:8]([N:3]1[CH2:4][CH2:5][CH2:6][CH:2]1[CH3:1])([CH3:10])[C:15]#[N:14]

Participants

7

Reactant 4

HCID 180AcetoneHCID 9032Potassium CyanideHCID 130032-MethylpyrrolidineHCID 105034Isocyanate

Product 1

HCID 593478232-Methyl-2-(2-methyl-1-pyrrolidinyl)propanenitrileYield 37.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred, ice-cooled mixture of 2-(RS)-methylpyrrolidine (4.25 g; 0.05 mol) and acetone (3.67 ml; 0.05 mol) was added a solution of potassium cyanide (3.25 g; 0.05 mol) in water (25 ml) dropwise over 10 min. After stirring at room temperature overnight, the crude reaction mixture was extracted with diethyl ether (2×200 ml) and the combined extracts washed with brine (200 ml), dried (Na2SO4) and evaporated under reduced pressure to afford a pale yellow oil. This was dissolved in DCM and PS-Isocyanate (4.5 g of resin loading 1.53 mmol/g) added. The mixture was stirred for 3 hours, filtered and the filtrate evaporated to afford the title compound as a colourless semi-solid (2.82 g; 37.5%). 1H NMR (CDCl3) δ(inter alia): 1.10 (3H, d), 1.45 (3H, s), 1.55 (3H, s), 1.75-2.00 (4H, m) 2.65 (1H, m) and 3.05-3.20 (2H, m).

Workup

  1. temperatureTo a stirred, ice-cooled
  2. customthe crude reaction mixture
  3. extractionwas extracted with diethyl ether (2×200 ml)
  4. washthe combined extracts washed with brine (200 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto afford a pale yellow oil
  8. stirringThe mixture was stirred for 3 hours
  9. filtrationfiltered
  10. customthe filtrate evaporated

Sources & evidence

ORD record
ord-6eda01cc9ea94c74a9311bbfab88dd4c
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Linked notes

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