Water → 4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)morpholine

HRID 2288033Notes

Reaction equation

HRID 2288033 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 192201-Benzyl-4-piperidone

Product 1

HCID 155575654-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)morpholineYield 100.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 10.0 g (52.9 mmol) of 1-benzyl-4-piperidone and 4.61 g (52.9 mmol) of morpholine in 100 ml of toluene was subjected to azeotropic dehydration for 5 hours under heating and reflux by using a water separator. After the 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 obtained in a quantitative yield. A solution of 1.52 g (34.6 mmol) of acetaldehyde in 20 ml of methylene chloride was cooled to -40° C. under an argon atmosphere, 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 1-benzyl-4-morpholino-1,2,5,6-tetrahydropyridine obtained above. After the completion of the dropwise addition, the temperature was raised gradually and the reaction mixture was allowed to stand overnight at room temperature. After the addition of water to terminate the reaction, the reaction mixture was extracted with methylene chloride. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated by evaporation 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 the completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2715c93643654a1d99d8d33541b47fe8
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

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