HCID 12891626, compound → HCID 88784466, compound

HRID 1856571Notes

Reaction equation

HRID 1856571 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33]CC4C=CC=CC=4)=[CH:29][CH:28]=3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[OH2:33].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)[CH2:23][CH2:24]2)=[CH:4][CH:3]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)[CH2:23][CH2:24]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12891626HCID 12891626, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 88784466HCID 88784466, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7.5 parts of 1-(4-fluorophenylmethyl)-N-[1-{2-[4-(phenylmethoxy)phenyl]ethyl}-4-piperidinyl]-1H-benzimidazol-2-amine and 120 parts of methanol is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is suspended in 2,2'-oxybispropane. The product is filtered off and dried, yielding 5.5 parts (88.5%) of 4-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]phenol hemihydrate; mp. 111.6° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. filtrationThe product is filtered off
  4. customdried

Sources & evidence

ORD record
ord-032bdfb268a64751bfaf1de955dc93a0
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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