HCID 15718798, compound → HCID 15718836, compound

HRID 2166133Notes

Reaction equation

HRID 2166133 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[N:19]([CH2:20][CH2:21][O:22][CH2:23][CH2:24][OH:25])[C:18]4[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=4[N:16]=3)[CH2:10][CH2:9]2)C=CC=CC=1.[H][H]>[Pd].CO>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:19]([CH2:20][CH2:21][O:22][CH2:23][CH2:24][OH:25])[C:18]3[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=3[N:16]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 15718798HCID 15718798, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15718836HCID 15718836, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 140 parts of 2-[2-[2-[[1-(phenylmethyl)-4-piperidinyl]amino]-1H-benzimidazol-1-yl]ethoxy]ethanol and 480 parts of methanol was hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off over diatomaceous earth and the filtrate was evaporated. The residue was crystallized twice from acetonitrile. The product was filtered off and dried, yielding 53.3 parts (46.0%) of 2-[2-[2-(4-piperidinylamino)-1H-benzimidazol-1-yl]ethoxy]ethanol; mp. 163.7° C. (compound 38).

Workup

  1. filtrationthe catalyst was filtered off over diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized twice from acetonitrile
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-b87302670ed0485a8ee504184673b104
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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