2-(Diisopropylamino)ethyl chloride → 4-Diisopropylamino-2-phenyl-butyronitrile

HRID 428336Notes

Reaction equation

HRID 428336 reaction equation
[H-].[Na+].[CH2:3]([C:10]#[N:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:13][CH2:14][N:15]([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17]>>[CH:16]([N:15]([CH:19]([CH3:21])[CH3:20])[CH2:14][CH2:13][CH:3]([C:10]#[N:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 73122-(Diisopropylamino)ethyl chlorideHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

Product 1

HCID 126122104-Diisopropylamino-2-phenyl-butyronitrile

Procedure

Sodium hydride, 80% in mineral oil (2.82 g, 94 mmol), was washed with petroleum ether and dried under a N2-stream. Dry DMF (100 mL) was added. Benzyl cyanide (12.1 g, 103 mmol) was added to the stirred suspension over a period of 20 min. The temperature rose to approx. 45° C. The mixture was stirred for another 15 min. 2-Chloroethyl-diisopropylamine (15.4 g, 94 mmol) was added. All the amine was consumed within 30 min. Most of the DMF was evaporated under reduced pressure and the residue was dissolved in water/diethyl ether. The aqueous phase was extracted once with diethyl ether and the combined organic phases were extracted twice with 2 M HCl. The combined aqueous phases were made alkaline (11 M NaOH) and extracted twice with diethyl ether. The combined organic phases were then dried (Na2SO4) and the solvent was evaporated. The crude product was chromatographed on silica (petroleum ether-triethylamine, 40:1), affording the title compound, 16.8 g (67%), as a colourless liquid. 1H NMR (CDCl3) δ1.01 (m, 12H), 1.97 (m, 2H), 2.62 (m, 2H), 3.00 (m, 2H), 4.02 (dd, 1H), 7.17-7.40 (m, 5H).

Workup

  1. customdried under a N2-stream
  2. additionDry DMF (100 mL) was added
  3. customrose to approx. 45° C
  4. customAll the amine was consumed within 30 min
  5. customMost of the DMF was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in water/diethyl ether
  7. extractionThe aqueous phase was extracted once with diethyl ether
  8. extractionthe combined organic phases were extracted twice with 2 M HCl
  9. extractionextracted twice with diethyl ether
  10. dry with materialThe combined organic phases were then dried (Na2SO4)
  11. customthe solvent was evaporated
  12. customThe crude product was chromatographed on silica (petroleum ether-triethylamine, 40:1)

Sources & evidence

ORD record
ord-8092e409baad4d118edf305d3390e14d
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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