Formaldehyde → 2-(1-Acetylpiperidin-4-yl)propenal

HRID 376140Notes

Reaction equation

HRID 376140 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][OH:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl-].[CH3:14][NH2+]C.C=O>>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10](=[CH2:14])[CH:11]=[O:12])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 12954980Dimethylazanium;chlorideHCID 21468226HCID 21468226, compound

Product 1

HCID 451192142-(1-Acetylpiperidin-4-yl)propenal

Procedure

3.95 g (23.3 mmol) of 2-(1-acetylpiperidin-4-yl)ethanol, 2.12 g (26.3 mmol) of dimethylammonium chloride and 3 ml (40 mmol) of 37% formaldehyde solution are heated at 110° C. for 2 hours with stirring. The mixture is allowed to cool and is extracted several times with diethyl ether. The organic phases are combined, washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated to dryness by evaporation. 2-(1-acetylpiperidin-4-yl)propenal is obtained in the form of a yellowish oil which can be further reacted without further purification.

Workup

  1. temperatureto cool
  2. extractionis extracted several times with diethyl ether
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-22529da802a84b0abbec516a97fb4203
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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