1,3-dihydro-1-{3-[4-(phenylmethyl)-1-piperazinyl]propyl}-2H-benzimidazol-2-one → 1,3-dihydro-1-[3-(1-piperazinyl)propyl]-2H-benzimidazol-2-one

HRID 2050286Notes

Reaction equation

HRID 2050286 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:10][CH2:9]2)C=CC=CC=1.[H][H]>[Pd].CO>[N:11]1([CH2:14][CH2:15][CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[NH:19][C:18]2=[O:26])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 205063601,3-dihydro-1-{3-[4-(phenylmethyl)-1-piperazinyl]propyl}-2H-benzimidazol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 131056231,3-dihydro-1-[3-(1-piperazinyl)propyl]-2H-benzimidazol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 63 parts of 1,3-dihydro-1-{3-[4-(phenylmethyl)-1-piperazinyl]propyl}-2H-benzimidazol-2-one in 400 parts of methanol is hydrogenated at normal pressure and at room temperature with 10 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off over hyflo and the filtrate is evaporated. The residue is crystallized from a mixture of 4-methyl-2-pentanone and 2-propanol. The product is filtered off and dried, yielding 1,3-dihydro-1-[3-(1-piperazinyl)propyl]-2H-benzimidazol-2-one; mp. 157.5° C.

Workup

  1. filtrationthe catalyst is filtered off over hyflo
  2. customthe filtrate is evaporated
  3. customThe residue is crystallized from a mixture of 4-methyl-2-pentanone and 2-propanol
  4. filtrationThe product is filtered off
  5. customdried

Sources & evidence

ORD record
ord-fb991ad01f2f42ce8c8c9a9476d97b09
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

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