HCID 178418361, compound → HCID 178474482, compound

HRID 437660Notes

Reaction equation

HRID 437660 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]3=[N:23][C:24](=[O:26])[CH3:25])[CH2:10][CH2:9]2)C=CC=CC=1.[H][H]>[Pd].CO>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]2=[N:23][C:24](=[O:26])[CH3:25])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178474483HCID 178474483, compound

Product 1

HCID 178474482HCID 178474482, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 12 parts of N-{1,3-dihydro-1-[1-(phenylmethyl)-4-piperidinyl]-2H-benzimidazol-2-ylidene}acetamide and 120 parts of methanol is hydrogenated at normal pressure and at room temperature with 5 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 2,2'-oxybispropane and 2-propanol. The product is filtered off and recrystallized from a mixture of ethanol and 2,2'-oxybispropane, yielding 2.6 parts of N-[1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-ylidene]acetamide; mp. 164.5° C.

Workup

  1. filtrationthe catalyst is filtered off over hyflo
  2. customthe filtrate is evaporated
  3. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol
  4. filtrationThe product is filtered off
  5. customrecrystallized from a mixture of ethanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-2669a13c8d834fad841bcaa6f96a6e01
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

Loading…