Benzaldehyde → HCID 15290694, compound

HRID 2257891Notes

Reaction equation

HRID 2257891 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-methoxymethoxy-piperidine 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-2ae60a8ac1cc433cb95fe585d841b3e1
Source dataset
uspto-grants-1997_08
Patent number
US05658926

Reaction notes

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