Benzaldehyde → HCID 15290694, compound

HRID 1720293Notes

Reaction equation

HRID 1720293 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:11][O:12][CH3:13])[CH2:6][CH2:5]1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C.[Pd]>[CH2:14]([NH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([O:10][CH2:11][O:12][CH3:13])[CH2:8][CH2:9]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 22923703HCID 22923703, compound

Product 1

HCID 15290694HCID 15290694, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

27 g of 1-(2-aminoethyl)-4-methoxymethoxypiperidine was dropwise added to a solution of 15 g of benzaldehyde in 300 ml of ethanol, at room temperature. The mixture was stirred at the same temperature for 1 day. To the reaction mixture was added 5 g of 10% Pd-C, and the resulting mixture was allowed to absorb hydrogen at room temperature at atmospheric pressure. After a reaction was over, the catalyst was removed by filtration. The filtrate was diluted with ethyl acetate. The dilution was subjected to extraction with 10% hydrochloric acid. The aqueous layer was made alkaline with an aqueous potassium hydroxide solution and then subjected to extraction with ethyl acetate. The extract was washed with water and dried with magnesium sulfate. The solvent was removed by distillation. The resulting residue was purified by a silica gel column chromatography (eluant: 10% methanol-chloroform) to obtain 25.50 g of 1-(2-benzylaminoethyl)-4-methoxymethoxypiperidine.

Workup

  1. customto absorb hydrogen at room temperature at atmospheric pressure
  2. customwas removed by filtration
  3. additionThe filtrate was diluted with ethyl acetate
  4. extractionThe dilution was subjected to extraction with 10% hydrochloric acid
  5. extractionsubjected to extraction with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent was removed by distillation
  9. customThe resulting residue was purified by a silica gel column chromatography (eluant: 10% methanol-chloroform)

Sources & evidence

ORD record
ord-d354411db17146f5a59b7888d81cc6ae
Source dataset
uspto-grants-1996_04
Patent number
US05506239

Reaction notes

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