Water → Ethyldiisopropylethylamine

HRID 374668Notes

Reaction equation

HRID 374668 reaction equation
[CH:1]([N:4]([CH:9]([CH3:11])[CH3:10])[CH:5]([CH3:8])[C:6]#N)([CH3:3])[CH3:2].[CH2:12]([Mg]Br)C.O>C(OCC)C>[CH:1]([N:4]([CH:5]([CH2:6][CH3:12])[CH3:8])[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 109972602-(Diisopropylamino)propionitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 18997630Ethyldiisopropylethylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-(diisopropylamino)propionitrile (25.00 g, 0.162 mol) in diethyl ether (20 ml) was added dropwise to a 1M solution of ethyl magnesium bromide in diethyl ether (32.4 ml, 0.324 mol) and the mixture was refluxed for 30 min. Water (25 ml) was added and white precipitate was filtered off and washed with diethyl ether (2×100 ml). The ether solutions were combined, dried over anhydrous magnesium sulfate and the product was isolated by distillation: 13.80 g, 51%, bp 60°-62° C./20 mm Hg. 1H NMR CDCl3 δ ppm, 0.85 (t, J=6.5 Hz, 3H, CH3) , 0.98 (d, J=6.5 Hz, 6H, CH3) 0.99 (d, J=6.5 Hz, 3H, CH3), 1.05 (d, J=6.5 Hz, 6H, CH3) , 1.17-1.44(m, 2H, CH2), 2.70 (m, 1H, CH), 3.08 (sep, J=6.5 Hz, 2H, CH).

Workup

  1. temperaturethe mixture was refluxed for 30 min
  2. filtrationwhite precipitate was filtered off
  3. washwashed with diethyl ether (2×100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe product was isolated by distillation

Sources & evidence

ORD record
ord-c0d7bf166159428fb422e6c482e76f6a
Source dataset
uspto-grants-1996_01
Patent number
US05481038

Reaction notes

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