Ethyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylate → 4-Piperidinecarboxylic acid, 4-(phenylamino)-, ethyl ester

HRID 1448280Notes

Reaction equation

HRID 1448280 reaction equation
[NH:1]([C:8]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)(=O)C>[NH:1]([C:8]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3017395Ethyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 122981724-Piperidinecarboxylic acid, 4-(phenylamino)-, ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 16.9 parts of ethyl 4-anilino-1-benzylisonipecotate in 150 parts of acetic acid is hydrogenated at normal pressure and at a temperature of 45° C. with 1.5 parts of palladium-on-charcoal 10%. After the calculated amount of hydrogen is taken up, the reaction mixture is allowed to cool to room temperature, the catalyst is filtered off and the filtrate is evaporated. The oily residue is taken up in water, alkalized with ammonium hydroxide and the product is extracted with chloroform. The extract is washed with water, dried, filtered and evaporated. The oily residue solidifies on triturating in petroleumether. The product is filtered off and crystallized from acetonitrile, yielding ethyl 4-anilinoisonipecotate; mp. 121.8° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. extractionthe product is extracted with chloroform
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customon triturating in petroleumether
  9. filtrationThe product is filtered off
  10. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-215307359159454daad783ac0fe4fce9
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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