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

HRID 487474Notes

Reaction equation

HRID 487474 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 21468226Ethanone,1-[4-(2-hydroxyethyl)-1-piperidinyl]-

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-604b3f2eec244a168750a5e227725d99
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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