Hydrochloric Acid → 1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]-1H-benzimidazole

HRID 1977254Notes

Reaction equation

HRID 1977254 reaction equation
O[C:2]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[CH:13]2)[CH2:4][CH2:3]1.Cl>C(O)C>[C:21]1([C:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[N:14]=[CH:13]3)[CH2:4][CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 154861071-[4-(4-hydroxy-4-phenyl-1-piperidyl)butyl]-1H-benzimidazole

Product 1

HCID 154861111-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]-1H-benzimidazoleYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 13.4 g (38.2 mmol) of 1-[4-(4-hydroxy-4-phenyl-1-piperidyl)butyl]-1H-benzimidazole, 150 ml of concentrated HCl and 75 ml of ethanol is heated at reflux for 6 hours. The ethanol is then evaporated and the aqueous solution is cooled, basified with dilute NaOH and extracted with chloroform. The organic phase is dried with anhydrous sodium sulfate and evaporated at reduced pressure, a crude product being obtained which is purified by chromatography on silica gel. 9.1 g (27.5 mmol) of 1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]-1H-benzimidazole are obtained.

Workup

  1. temperatureat reflux for 6 hours
  2. customThe ethanol is then evaporated
  3. temperaturethe aqueous solution is cooled
  4. extractionextracted with chloroform
  5. dry with materialThe organic phase is dried with anhydrous sodium sulfate
  6. customevaporated at reduced pressure
  7. customa crude product being obtained which
  8. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-44de5e1c8e604aac82b84e1d361d0586
Source dataset
uspto-grants-2001_05
Patent number
US06232329B1

Reaction notes

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