2-(Methylamino)ethanol → 3-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-benzonitrile

HRID 219905Notes

Reaction equation

HRID 219905 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Br[CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12]>C(Cl)Cl>[OH:5][CH2:4][CH2:3][N:2]([CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12])[CH3:1]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 391615223-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-benzonitrileYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(methylamino)ethanol (4 mL, 51 mmol) and TEA (4 mL, 28.05 mmol) in DCM (75 mL) under N2, was added 3-(bromomethyl)benzonitrile (5 g, 25.50 mmol) at 0° C. and the mixture was stirred at RT for 30 min. After this time, reaction mixture was concentrated under reduced pressure and the remaining residue was dissolved in DCM and washed with water to give the title compound as a colorless liquid (4.9 g, 100%). 1H NMR (DMSO-d6, 400 MHz) δ 7.76 (s, 1H), 7.69-7.71 (m, 2H), 7.63-7.65 (m, 1H), 7.49-7.53 (m, 1H), 4.41-4.43 (m, 1H), 3.47-3.51 (m, 2H), 3.32 (m, 2H), 2.40-2.43 (m, 2H), 2.13 (s, 3H).

Workup

  1. customAfter this time, reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe remaining residue was dissolved in DCM
  4. washwashed with water

Sources & evidence

ORD record
ord-0735475729764e33835f7c071b00e909
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

Loading…