HCID 15096799, compound → HCID 15096813, compound

HRID 345598Notes

Reaction equation

HRID 345598 reaction equation
C1(C[O:8][C@H:9]2[C@H:14]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12][N:11](CC3C=CC=CC=3)[CH2:10]2)C=CC=CC=1.[H][H]>[Pd].CO>[OH:8][C@H:9]1[C@H:14]([NH:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12][NH:11][CH2:10]1

Participants

5

Reactant 2

HCID 15096799HCID 15096799, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15096813HCID 15096813, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 22.9 parts of trans-N-[3-(phenylmethoxy)-1-(phenylmethyl)-4-piperidinyl]benzamide in 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 3 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and suspended in trichloromethane. The whole was shaken with a dilute ammonium hydroxide solution and the layers were separated. The aqueous phase was evaporated and the solid residue was suspended in 5 parts of water. The product was filtered off and dried, yielding 6 parts of trans-N-(3-hydroxy-4-piperidinyl)benzamide; mp. 210° C. (compound 218).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. filtrationThe product was filtered off
  4. customthe layers were separated
  5. customThe aqueous phase was evaporated
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-371e327c78fc46da88c0671396306a37
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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