Benzaldehyde → (1H-imidazol-2-yl)-[1-(phenylmethyl)-4-piperidinyl]methanone

HRID 2210805Notes

Reaction equation

HRID 2210805 reaction equation
Br.Br.[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[C:8]([CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:9].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(=O)C.[K+].S1C=CC=C1.[H][H]>CO.[Pd]>[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[C:8]([CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[O:9]

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 8030ThiopheneHCID 517044Potassium AcetateHCID 69954498HCID 69954498, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19377728(1H-imidazol-2-yl)-[1-(phenylmethyl)-4-piperidinyl]methanoneYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 34 g of (1 H-imidazol-2-yl)(4-piperidinyl)methanone dihydrobromide, 20 g of benzaldehyde and 15 g of potassium acetate in 500 ml of methanol and 1 ml of a solution of thiophene in methanol (4%) was hydrogenated at normal pressure and at 50° C. in the presence of 3 g of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the flitrate was evaporated. The residue was partitioned between dichloromethane and NH4Cl (aq.). The aqueous layer was extracted with dichloromethane and the combined organic layers were dried, filtered and evaporated. The residue was taken up in water, acidified with hydrochloric acid and washed twice with 2,2'-oxybispropane. The aqueous layer was basified with NaOH 50% and extracted three times with dichloromethane. The combined organic layers were dried, filtered and evaporated. The residue was stirred in 2,2'-oxybispropane, filtered off and dried, yielding 22.3 g (83%) of (1H-imidazol-2-yl)-[1-(phenylmethyl)-4-piperidinyl]methanone; mp. 121.0° C. (interm. 27);

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe flitrate was evaporated
  3. customThe residue was partitioned between dichloromethane and NH4Cl (aq.)
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. customthe combined organic layers were dried
  6. filtrationfiltered
  7. customevaporated
  8. washwashed twice with 2,2'-oxybispropane
  9. extractionextracted three times with dichloromethane
  10. customThe combined organic layers were dried
  11. filtrationfiltered
  12. customevaporated
  13. filtrationfiltered off
  14. customdried

Sources & evidence

ORD record
ord-c5cd94b122d4477295e313c16cae7f3a
Source dataset
uspto-grants-1995_10
Patent number
US05461050

Reaction notes

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