2-Methoxyethylamine → HCID 28425848, compound

HRID 219897Notes

Reaction equation

HRID 219897 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.Br[CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19]>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 28425848HCID 28425848, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-methoxyethylamine (5.73 mL, 0.0612 mol) and triethylamine (4.05 mL, 0.0306 mol) in dry DCM (100 mL), was added 3-(bromomethyl)benzonitrile (6 g, 0.0306 mol) in portions over a period of 10 min at 0° C. After being stirred at RT for 5 h, the reaction mixture washed with water (2×100 mL), dried using sodium sulphate and concentrated under reduced pressure. The obtained crude was purified using column chromatography on silica gel (chloroform/methanol) to afford the title compound as a pale yellow liquid (5 g, 86%). 1H NMR (DMSO-d6, 400 MHz) δ 7.75 (s, 1H), 7.64-7.68 (m, 2H), 7.48-7.52 (m, 1H), 3.73 (s, 2H), 3.35-3.38 (m, 2H), 3.21 (s, 3H), 2.59-2.61 (m, 2H).

Workup

  1. washthe reaction mixture washed with water (2×100 mL)
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained crude
  5. customwas purified

Sources & evidence

ORD record
ord-3eccdb552e8c4d0792130e0acdff6ea0
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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