Acrylonitrile → 3-(Cyclobutylamino)propionitrile

HRID 1776249Notes

Reaction equation

HRID 1776249 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.[C:6](#[N:9])[CH:7]=[CH2:8]>CO>[CH:1]1([NH:5][CH2:8][CH2:7][C:6]#[N:9])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 75645Cyclobutylamine

Product 1

HCID 183489093-(Cyclobutylamino)propionitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature, cyclobutylamine (5.90 mL, 59.8 mmol) was added dropwise, over 15 mins, to a solution of acrylonitrile (4.76 g, 89.7 mmol) in methanol (7 mL). The mixture was stirred at room temperature for 30 mins and at reflux for 1 hr, cooled to room temperature, concentrated under reduced pressure. The desired product was obtained by distillation under vacuum to provide a clear liquid (7.7 g, 98%). 1H NMR (CDCl3, 300 MHz) δ 3.29-3.21 (m, 1H), 2.88-2.83 (t, 2H, J=6.6 Hz), 2.50-2.46 (t, 2H, J=6.6 Hz), 2.26-2.20 (m, 2H), 1.76-1.63 (m, 4H), 1.30 (br s, 1H).

Workup

  1. temperatureat reflux for 1 hr
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44984cd4b7d54719b2587f7e40b3496d
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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