Nitrogen → 4-((3-Hydroxypropyl)amino)benzonitrile

HRID 2180012Notes

Reaction equation

HRID 2180012 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][OH:14].N#N.O>C(OCC)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:3][CH:4]=1)#[N:7]

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 90863-Amino-1-propanolHCID 145174-Fluorobenzonitrile

Product 1

HCID 218676634-((3-Hydroxypropyl)amino)benzonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-fluorobenzonitrile (1.0 g, 8.26 mmol) and 3-aminopropanol (4.54 g, 58.7 mmol) was refluxed under an inert atmosphere (N2) for 15 h. Water (500 mL) and diethyl ether (500 mL) were then added, and the resulting organic layer separated, dried (Na2SO4) and concentrated. The residue was purified by column chromatography (heptane:EtOAc; 1:3) to give the sub-title compound in 84% yield.

Workup

  1. customthe resulting organic layer separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (heptane:EtOAc; 1:3)

Sources & evidence

ORD record
ord-449aec441f5a4fbaa22005e375bf7cc3
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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