N-(4-(4-(Phenylmethyl)-1-piperazinyl)phenyl)acetamide → N-[4-(1-Piperazinyl)phenyl]acetamide

HRID 1639074Notes

Reaction equation

HRID 1639074 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)C=CC=CC=1>CO.[Pd]>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:18][CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 960610N-(4-(4-(Phenylmethyl)-1-piperazinyl)phenyl)acetamide

Product 1

HCID 15631761N-[4-(1-Piperazinyl)phenyl]acetamideYield 56.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

This compound was prepared by the hydrogenation of 7.7 g (0.025 mole) of N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]acetamide in 100 ml of methanol using palladium on carbon as the catalyst. The solution was filtered and the filtrate concentrated under reduced pressure to give an oil which crystallized. The solid was dissolved in a minimum amount of a methylene chloride/10% methanol solution and passed through a 100 g Florisil® column. The desired frations were concentrated to an oil under reduced pressure which crystallized to give 3.1 g (56%) of crude product. A 0.5 g portion was recrystallized from methanol/petroleum ether to give cream colored solid, m.p. 191°-193° C.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give an oil which
  4. customcrystallized
  5. dissolutionThe solid was dissolved in a minimum amount of a methylene chloride/10% methanol solution
  6. concentrationThe desired frations were concentrated to an oil under reduced pressure which
  7. customcrystallized

Sources & evidence

ORD record
ord-5116b17c21cc490db5780c61df41599f
Source dataset
uspto-grants-1989_11
Patent number
US04882330

Reaction notes

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