Cyclopentylamine → 3-(Cyclopentylamino)propionitrile

HRID 1776251Notes

Reaction equation

HRID 1776251 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7](#[N:10])[CH:8]=[CH2:9]>CO>[CH:1]1([NH:6][CH2:9][CH2:8][C:7]#[N:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 7855Acrylonitrile

Product 1

HCID 27580023-(Cyclopentylamino)propionitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature, cyclopentylamine (5.794 mL, 58.7 mmol) was added dropwise to a solution of acrylonitrile (5.79 mL, 88.1 mmol) in methanol (7 mL). The solution was stirred at room temperature for 30 mins and at reflux for 1 hr, cooled to room temperature, and concentrated under reduced pressure. The desired product as obtained by distillation under vacuum to provide a clear liquid (7.4 g, 91%). 1H NMR (CDCl3, 300 MHz) δ 3.14-3.04 (quint, 1H, J=6.3 Hz), 2.91-2.87 (t, 2H, J=6.9 Hz), 2.53-2.48 (td, 2H, J=0.9, 6.9 Hz), 1.88-1.78 (m, 2H), 1.73-1.49 (m, 4H), 1.36-1.24 (m, 2H), 1.19 (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-73eabb53c58b452e84ecebb1476e5efb
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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