Borane;tetrahydrofuran → 2-(2-Chlorophenyl)propan-1-amine

HRID 1853907Notes

Reaction equation

HRID 1853907 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:11])[C:9]#[N:10].B.C1COCC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:11])[CH2:9][NH2:10]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 126365722-(2-Chlorophenyl)propanenitrile

Product 1

HCID 132903012-(2-Chlorophenyl)propan-1-amineYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(2-chlorophenyl)propanenitrile (14 g, 84.8 mmol) in toluene at 0° C. was added BH3.THF (127, 255 mmol) and the reaction was warmed to room temperature and heated at reflux for 4 h. The reaction mixture was cooled; quenched with water, concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (13.9 g, 97%) as a reddish oil: ESI MS m/z 170 [C9H12ClN+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. temperatureThe reaction mixture was cooled
  4. customquenched with water
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-439f7682f6ea4dbca591036cc30e14c7
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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