Ethanolamine → 4-[3-(2-Hydroxyethylamino)propyl]benzonitrile

HRID 899133Notes

Reaction equation

HRID 899133 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.[CH2:13]([CH2:15][NH2:16])[OH:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:14][CH2:13][CH2:15][NH:16][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 4583644-(3-Bromopropyl)benzonitrile

Product 1

HCID 690715794-[3-(2-Hydroxyethylamino)propyl]benzonitrileYield 82.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-(3-Bromopropyl)benzonitrile (20 g, 0.089 mol) in acetonitrile was added to a vigorously stirred mixture of ethanolamine (27.2 g, 0.447 mol) and potassium carbonate (18.5 g, 0.133 mol) in 300 mL of dry acetonitrile. Stirring was then continued at room temperature overnight under a nitrogen atmosphere. The reaction mixture was filtered and concentrated under reduced pressure. The crude product thereby obtained was purified by column chromatography (using methanol in chloroform) to yield 15 g of the sub-title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product thereby obtained
  4. customwas purified by column chromatography (using methanol in chloroform)

Sources & evidence

ORD record
ord-0f28dc3322c4467c844dcfd008192dd3
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

Loading…