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

HRID 899116Notes

Reaction equation

HRID 899116 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.C([O-])([O-])=O.[K+].[K+].[CH2:19]([CH2:21][NH2:22])[OH:20]>C(#N)C>[OH:20][CH2:19][CH2:21][NH:22][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 57.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution 4-(3-bromopropyl)benzonitrile (8 g, 0.0357 mol; see step (iv) above) in dry acetonitrile (150 mL) were added anhydrous K2CO3 (7.4 g, 0.0535 mol) and ethanolamine (10.9 g, 0.179 mol). The resulting reaction mixture was then stirred overnight at room temperature, after which it was filtered and concentrated. The crude product thus obtained was purified by column chromatography over silica gel, using methanol in chloroform as eluent, to yield 4.2 g (57.5%) of the sub-title compound as a pale yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. filtrationafter which it was filtered
  3. concentrationconcentrated
  4. customThe crude product thus obtained
  5. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-3d440c14301246ca95306f3c3a98cce4
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

Loading…