Thiophene → 1-[3-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]butyl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 126873Notes

Reaction equation

HRID 126873 reaction equation
S1C=CC=C1.O=[C:7]([CH3:20])[CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19].Cl.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:37])[CH2:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+].[H][H]>[Pd].CO.C(O)C>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:37])[CH2:30][CH:31]2[CH2:36][CH2:35][N:34]([CH:7]([CH3:20])[CH2:8][CH2:9][N:10]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[NH:12][C:11]3=[O:19])[CH2:33][CH2:32]2)=[CH:25][CH:24]=1

Participants

9

Reactant 5

HCID 8030ThiopheneHCID 516892Sodium BicarbonateHCID 202880421,3-dihydro-1-(3-oxobutyl)-2H-benzimidazol-2-oneHCID 20288069HCID 20288069, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 202880401-[3-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]butyl]-1,3-dihydro-2H-benzimidazol-2-oneYield 33%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 1 part of a volume of 2 parts of thiophene in 40 parts of ethanol are added 4.1 parts of 1,3 -dihydro-1-(3-oxobutyl)-2H-benzimidazol-2-one, 5.2 parts of 1-(4-fluorophenyl)-2-(4-piperidinyl)ethanone hydrochloride, 2 parts of sodium hydrogen carbonate and 160 parts of methanol. The whole is hydrogenated in the Parr-apparatus at 60° C. 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 allowed to crystallize. The product is filtered off and dried, yielding 2.7 parts (33%) of 1-[3-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]butyl]-1,3-dihydro-2H-benzimidazol-2-one; mp. 185.4° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customto crystallize
  3. filtrationThe product is filtered off
  4. customdried

Sources & evidence

ORD record
ord-ff68b46f73944d309e60da67cc9180a7
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

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