1-Phenylcyclopropanecarbonitrile → 1-Phenylcyclopropanemethanamine

HRID 2282832Notes

Reaction equation

HRID 2282832 reaction equation
[C:1]1([C:7]2([C:10]#[N:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([C:7]2([CH2:10][NH2:11])[CH2:8][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 702881-PhenylcyclopropanecarbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 702871-Phenylcyclopropanemethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-phenylcyclopropanecarbonitrile (50 g, 0.34 mol, 1 eq.) in tetrahydrofuran (500 mL, 0.7 M) at 0° C. was added lithium aluminum hydride (23 g, 0.35 mol, 1.03 eq.). The reaction mixture was stirred at 0° C. for one hour and then at reflux for one hour. The reaction mixture was then cooled down and quenched with water (23 mL) and a 15% aqueous sodium hydroxide solution (69 mL). The mixture was filtered and concentrated in vacuo to afford #@1 (36 g, 72%). LC-MS: m/z 148.1 [M+H+], retention time=0.86 minutes; 1H NMR (400 MHz, CDCl3) δ 7.2-7.4 (m, 5H), 2.78 (s, 2H), 1.19 (br s, 2H), 0.72-0.84 (m, 4H).

Workup

  1. temperatureat reflux for one hour
  2. temperatureThe reaction mixture was then cooled down
  3. customquenched with water (23 mL)
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customto afford #@1 (36 g, 72%)

Sources & evidence

ORD record
ord-ae1a71e6b9c7459793c31afbb2609f67
Source dataset
uspto-grants-2015_09
Patent number
US09138486B2

Reaction notes

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