1-Benzyl-4-(methoxymethyl)-N-phenylpiperidin-4-amine → 4-(Methoxymethyl)-N-phenylpiperidin-4-amine

HRID 1973800Notes

Reaction equation

HRID 1973800 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9][CH2:8][N:7](CC2C=CC=CC=2)[CH2:6][CH2:5]1.[H][H]>[Pd].C(O)(=O)C>[CH3:1][O:2][CH2:3][C:4]1([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 30477241-Benzyl-4-(methoxymethyl)-N-phenylpiperidin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 183199324-(Methoxymethyl)-N-phenylpiperidin-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 10 parts of 4-(methoxymethyl)-N-phenyl-1-(phenylmethyl)-4-piperidinamine and 200 parts of acetic acid is hydrogenated at normal pressure and at room temperature with 2parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The oily residue is dissolved in water, cooled and alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 10% of methanol, saturated with gaseous ammonia, as eluent. The pure fractions are collected and the eluent is evaporated, yielding 4-(methoxymethyl)-N-phenyl-4-piperidinamine as an oily residue.

Workup

  1. customis hydrogenated at normal pressure and at room temperature
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. dissolutionThe oily residue is dissolved in water
  5. temperaturecooled
  6. extractionThe product is extracted with trichloromethane
  7. washThe extract is washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe oily residue is purified by column-chromatography over silica gel using
  12. additiona mixture of trichloromethane and 10% of methanol
  13. customThe pure fractions are collected
  14. customthe eluent is evaporated

Sources & evidence

ORD record
ord-757428b50b924807a582cd232e568690
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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