Acetaldehyde → HCID 69353622, compound

HRID 2228246Notes

Reaction equation

HRID 2228246 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].[O:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.[CH2:20](N(CC)CC)[CH3:21].C(=O)C>ClCCCl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][CH2:20][CH2:21][CH:16]2[CH2:17][CH2:18][O:13][CH2:14][CH2:15]2)=[CH:11][CH:12]=1)([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 8471TriethylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 69353622HCID 69353622, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In 1,2-dichloroethane (50 ml) were suspended p-nitrobenzylaminehydrochloride (3.77 g), 4H-tetrahydropyran-4-one (2 g) and triethylamine (2.8 ml), and to the mixture was added, under ice-cooling, triacetoxy sodium boron hydride (5.92 g). Under nitrogen atmosphere, the mixture was stirred at room temperature for 4 hours, and to the mixture were added, under ice-cooling, acetaldehyde (1.5 ml) and triacetoxy sodium boron hydride (5.92 g). Under nitrogen atmosphere, the mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was neutralized with sodium hydroxide solution. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give N-(4-nitrobenzyl)-N-(tetrahydropyran-4-yl)ethylamine (4.0 g) as yellow oil. 1H-NMR(δ ppm, CDCl3) 1.01 (3H, t, J=6.9 Hz), 1.52-1.73 (4H, m), 2.59 (2H, q, J=6.9 Hz), 2.68-2.83 (1H, m), 3.34 (2H, dt, J=3.6, 11.2 Hz), 3.73 (2H, s), 3.99-4.06 (2H, m), 7.54 (2H, d, J=9.0 Hz), 8.16 (2H, d, J=9.0 Hz). IR(neat) ν: 2951, 2841, 1599, 1520 cm−1.

Workup

  1. additionto the mixture was added, under ice-
  2. temperaturecooling
  3. additionto the mixture were added, under ice-
  4. temperaturecooling
  5. stirringUnder nitrogen atmosphere, the mixture was stirred at room temperature overnight
  6. customThe solvent was evaporated
  7. extractionThe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customUnder reduced pressure, the solvent was evaporated
  11. customthe residue was purified with silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-65ac611081ce48ef9f6224c56cf7efda
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

Loading…