Hydrochloric Acid → HCID 86685922, compound

HRID 2277586Notes

Reaction equation

HRID 2277586 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:11])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.C(O)C.Cl.O>C1COCC1.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:11])[CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 5526435314271-35-3

Product 1

HCID 86685922HCID 86685922, compoundYield 115.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-chloro-phenyl)-propionitrile (5.0 g, 30.2 mmol) in THF (80 mL) was added borane-tetrahydrofuran complex solution (45 mL, 45.3 mmol). The reaction mixture was stirred at room temperature overnight. Ethanol (10 mL) was then added to the reaction mixture; after stirring at room temperature for 20 min, a solution of HCl in ether (2 M, 12.5 mL) was added. After stirring for another 1 hour, water was added to induce the precipitation of the product. The white solid was collected by filtration and dried in vacuo to give the title compound (3.6 g, 70%). MS (for free amine): 170.1 (M+H+).

Workup

  1. stirringafter stirring at room temperature for 20 min
  2. stirringAfter stirring for another 1 hour
  3. customthe precipitation of the product
  4. filtrationThe white solid was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-14e24e35d5ca4e879b81c23c9b87dbfa
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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