1-[3-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]propyl]-4-(phenylmethyl)piperazine → 1-[3-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]propyl]piperazine

HRID 1030889Notes

Reaction equation

HRID 1030889 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:28]=[CH:27][C:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17](CC3C=CC=CC=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1.[H][H]>[Pd].CO>[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 149891781-[3-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]propyl]-4-(phenylmethyl)piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 149891791-[3-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]propyl]piperazineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 56 parts of 1-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]-4-(phenylmethyl)piperazine and 480 parts of methanol was hydrogenated at normal pressure and at 50° C. with 5 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 taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 46.9 parts (100%) of 1-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]piperazine as a residue (int. 16).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0e334ab19390416dade52cd7cd51d43e
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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