Benzaldehyde → HCID 178521301, compound

HRID 517655Notes

Reaction equation

HRID 517655 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CO>[CH:5](=[N:4]/[CH2:3][CH2:1][OH:2])\[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 700Ethanolamine

Product 1

HCID 178521301HCID 178521301, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethanolamine (1.23 g, 20.1 mmol) in anhydrous MeOH (50 mL) at 0° C. was added benzaldehyde (2.13 g, 20.0 mmol) and molecular sieves (10 pieces). The resulting mixture was gradually warmed to room temperature and stirred for 120 h. The reaction mixture was filtered while rinsing with CH2Cl2. The filtrate was evaporated, and the residue was dried under vacuum overnight to afford off-white oily Compound 1 (2.63 g, 87%). The compound was used for the next step without further purification. 1H NMR (CDCl3) δ 2.40 (s, 1H), 3.70 to 3.80 (m, 2H), 3.85 to 4.0 (m, 2H), 7.35 to 7.50 (m, 3H), 7.68 to 7.79 (m, 2H), 8.32 (s, 1H); 8.11 (d, 2H); 13C NMR (CDCl3) δ 62.28, 63.17, 128.1, 128.52, 130.78, 135.72, 163.10.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwhile rinsing with CH2Cl2
  3. customThe filtrate was evaporated
  4. customthe residue was dried under vacuum overnight

Sources & evidence

ORD record
ord-986b9e86dd2e4c86b71ba985e864a91a
Source dataset
uspto-grants-2015_08
Patent number
US09115094B2

Reaction notes

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