Acetaldehyde → HCID 23000816, compound

HRID 397608Notes

Reaction equation

HRID 397608 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CC[O:18][CH2:17][CH2:16]1.C(=O)C.C(N1CCC(N2CCOCC2)=CC1)C1C=CC=CC=1>O.C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH:17]([OH:18])[CH3:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 8083MorpholineHCID 192201-Benzyl-4-piperidoneHCID 155575654-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)morpholine

Product 1

HCID 23000816HCID 23000816, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A 100 ml tolune solution of 10.0 g (52.9 mmol) of 1-benzyl-4-piperidone and 4.61 g (52.9 mmol) of morpholine was subjected to azeotropic dehydration for 5 hours under heating and reflux by using a water separator. After completion of the reaction, the solvent was distilled off under reduced pressure, whereby 13.7 g of 1-benzyl-4-morpholino-1,2,5,6-tetrahydropyridine were quantitatively obtained. In an argon atmosphere, a 20 ml methylene chloride solution of 1.52 g (34.6 mmol) of acetaldehyde was cooled to −40° C., followed by the dropwise addition of 5.3 ml (43 mmol) of a boron trifluoride-ether complex and 7.44 g (28.8 mmol) of the 1-benzyl-4-morpholino-1,2,5,6-tetrahydropyridine obtained above. After completion of the dropwise addition, the temperature was gradually raised and the reaction mixture was allowed to stand overnight at room temperature. Water was added to terminate the reaction, followed by extraction with methylene chloride. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=4/1), whereby 4.68 g (yield: 69.7%) of 1-benzyl-3-(1-hydroxyethyl)-4-piperidone were obtained as a yellowish brown oil.

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure, whereby 13.7 g of 1-benzyl-4-morpholino-1,2,5,6-tetrahydropyridine
  5. customwere quantitatively obtained
  6. customobtained above
  7. additionAfter completion of the dropwise addition
  8. temperaturethe temperature was gradually raised
  9. customto terminate
  10. customthe reaction
  11. extractionfollowed by extraction with methylene chloride
  12. washThe organic layer was washed with saturated saline
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationconcentrated under reduced pressure
  15. washThe residue was subjected to chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-e8e1b8fb2a8445b88e97e51ccece0f9a
Source dataset
uspto-grants-2003_08
Patent number
US06610708B1

Reaction notes

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