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

HRID 1374082Notes

Reaction equation

HRID 1374082 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-4016c6d5da9a4072ab7b83b5fc18512b
Source dataset
uspto-grants-2007_01
Patent number
US07164017B2

Reaction notes

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