3-Amino-1-propanol → 4-((3-Hydroxypropyl)amino)benzonitrile

HRID 411135Notes

Reaction equation

HRID 411135 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]>O>[OH:14][CH2:13][CH2:12][CH2:11][NH:10][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 145174-Fluorobenzonitrile

Product 1

HCID 218676634-((3-Hydroxypropyl)amino)benzonitrileYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-fluorobenzonitrile (12.0 g, 99.1 mmol) and 3-amino-1-propanol (59.6 g, 793 mmol) was stirred at 80° C. under an inert atmosphere for 3 hours before water (150 mL) was added. The mixture was allowed to cool to rt, and was then extracted with diethyl ether. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo to yield 17 g (97%) of the title compound as an oil that crystallised upon standing.

Workup

  1. additionwas added
  2. extractionwas then extracted with diethyl ether
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e97ef9354af4d1680bfd88b12d01559
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

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