Methanol → HCID 12118765, compound

HRID 426050Notes

Reaction equation

HRID 426050 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1.CO>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 2875943-(3-Chloroanilino)propanenitrile

Product 1

HCID 12118765HCID 12118765, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(3-chlorophenylamino)propanenitrile (2 g, 0.011 mol) was dissolved in anhydrous THF (20 mL) and heated to reflux under nitrogen. A solution of BH3.MeS in THF was added drop wise and stirred at reflux overnight. The resulting solution was cooled to room temperature. Methanol was added drop wise to quench the reaction. After evaporation of the solution, the crude product was purified by column chromatography to afford the pure product N1-(3-chlorophenyl)propane-1,3-diamine (1.89 g, yield 95%)

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen
  3. temperatureat reflux overnight
  4. customto quench
  5. customthe reaction
  6. customAfter evaporation of the solution
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c150497601794101a4cd0f4a8fcc99d0
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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