ethyl 4-[2-[1-(phenylmethyl)-4-piperidinyl]ethoxy]benzoate (Z)-2-butenedioate → Ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate butanedioate

HRID 981623Notes

Reaction equation

HRID 981623 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].C1(C[N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][O:24][C:25]3[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)C=CC=CC=1.[H][H]>[Pd].C(O)C>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[NH:16]1[CH2:17][CH2:18][CH:19]([CH2:22][CH2:23][O:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:34][CH:35]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 86744608ethyl 4-[2-[1-(phenylmethyl)-4-piperidinyl]ethoxy]benzoate (Z)-2-butenedioateHCID 178418361HCID 178418361, compound

Product 1

HCID 23056112Ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate butanedioateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.8 parts of ethyl 4-[2-[1-(phenylmethyl)-4-piperidinyl]ethoxy]benzoate (Z)-2-butenedioate(1:1) and 120 parts of ethanol was hydrogenated at normal pressure and at 50° C. with 2 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 crystallized from 2-propanol, yielding 4.5 parts (100%) of ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate butanedioate(1:1); mp. 146.7° C. (int. 51).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-db55efe36a49452e8608929b48176e0f
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

Loading…