Ethanolamine → HCID 28878615, compound

HRID 219895Notes

Reaction equation

HRID 219895 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=O)#[N:6].[BH4-].[Na+]>C1(C)C=CC=CC=1>[OH:2][CH2:1][CH2:3][NH:4][CH2:10][C:9]1[CH:8]=[C:7]([CH:14]=[CH:13][CH:12]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 90670m-FormylbenzonitrileHCID 4311764Sodium borohydride

Product 1

HCID 28878615HCID 28878615, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred solution of ethanolamine (2.32 g, 0.0381 mol) in toluene (100 mL), was added 3-cyanobenzaldehyde (5 g, 0.0381 mol) under N2 and refluxed at 140° C. After complete distilling out of toluene, the reaction mass was cooled to RT and dissolved in dry methanol (100 mL). To this solution was added in portions sodium borohydride (2.17 g, 0.0571 mol) at 0° C. The reaction mass was evaporated under pressure, washed with water (100 mL), extracted in DCM (100 mL), dried using sodium sulphate and concentrated under reduced pressure. The obtained crude was purified using column chromatography on silica and chloroform/methanol as eluent to afford the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 7.76 (s, 1H), 7.65-7.69 (m, 2H), 7.49-7.52 (m, 1H), 4.45-4.48 (m, 1H), 3.74 (s, 2H), 3.42-3.46 (m, 2H), 2.51-2.54 (m, 2H).

Workup

  1. distillationAfter complete distilling out of toluene
  2. temperaturethe reaction mass was cooled to RT
  3. dissolutiondissolved in dry methanol (100 mL)
  4. customThe reaction mass was evaporated under pressure
  5. washwashed with water (100 mL)
  6. extractionextracted in DCM (100 mL)
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained crude
  10. customwas purified

Sources & evidence

ORD record
ord-e204b227048943d9b811affb277eb2d0
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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