Ethanolamine → HCID 28878615, compound

HRID 2410525Notes

Reaction equation

HRID 2410525 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[CH2:11]([CH2:13][NH2:14])[OH:12].C(=O)(O)[O-].[Na+]>C(#N)C>[OH:12][CH2:11][CH2:13][NH:14][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 28878615HCID 28878615, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(Bromomethyl)benzonitrile (20.0 g, 0.125 mol) was added portion wise into a mixture of ethanolamine (11.4 g, 0.19 mol) and sodium bicarbonate (21.0 g, 0.25 mol) in ACN (200 mL) at 0° C. The resulting mixture was stirred for 4 hours. The reaction mixture was concentrated under vacuum. The residue was taken up with water and extracted with DCM (200 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by chromatography to afford the title compound as white solid (9.8 g, 54%). 1H NMR (DMSO-d6, 400 MHz) δ 7.76 (s, 1H), 7.67 (m, 2H), 7.51 (m, 1H), 4.47 (brs, 1H), 3.74 (s, 2H), 3.44 (m, 2H), 2.51 (m, 2H), 2.12 (brs, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. extractionextracted with DCM (200 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-faeb955ef70f4a379facd14184c87596
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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