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

HRID 1351120Notes

Reaction equation

HRID 1351120 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

Alternative 1 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 room temperature, 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 sub-title compound as an oil that crystallised upon standing.

Workup

  1. additionwas added The mixture
  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-e88dddd542c245aa9a9fd632764897cd
Source dataset
uspto-grants-2007_05
Patent number
US07217708B2

Reaction notes

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