Thiophene → (1H-Benzoimidazol-2-yl)-(1-methyl-piperidin-4-yl)-amine

HRID 2166127Notes

Reaction equation

HRID 2166127 reaction equation
Br.Br.[NH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]=2)[CH2:5][CH2:4]1.S1C=CC=[CH:20]1.[OH-].[K+].[H][H]>CO.[Pd]>[CH3:20][N:3]1[CH2:4][CH2:5][CH:6]([NH:9][C:10]2[NH:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:7][CH2:8]1

Participants

8

Reactant 5

HCID 8030ThiopheneHCID 14797Potassium HydroxideHCID 22036968N-(Piperidin-4-yl)-1H-benzo[d]imidazol-2-amine dihydrobromideHCID 178418361HCID 178418361, compoundHCID 178486302HCID 178486302, compound

Product 1

HCID 14677578(1H-Benzoimidazol-2-yl)-(1-methyl-piperidin-4-yl)-amineYield 59.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 36.6 parts of N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide, 10 parts of poly(oxymethylene), 2 parts of a solution of thiophene in methanol 4%, 200 parts of methanol and 20 parts of potassium hydroxide was hydrogenated at normal pressure and at room temperature with 4 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was treated with a sodium hydroxide solution. The precipitated product was filtered off and dried, yielding 13.7 parts (59.4%) of N-(1-methyl-4-piperidinyl)-1H-benzimidazol-2-amine (interm 30).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionThe residue was treated with a sodium hydroxide solution
  4. filtrationThe precipitated product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-247f105c6b2f43c5a73bdd89eb048baf
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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