Trifluoroacetic acid → 1-(Piperidin-4-yl)-3-propyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 1870596Notes

Reaction equation

HRID 1870596 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:23][CH2:24][CH3:25])[C:15]2=[O:26])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:23]([N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:15]1=[O:26])[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 158951341-t-Butoxycarbonyl-4-(3-propyl-2-oxo-1-benzimidazolinyl)piperidine

Product 1

HCID 158951351-(Piperidin-4-yl)-3-propyl-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-t-butoxycarbonyl-4-(3-propyl-2-oxo-1-benzimidazolinyl)piperidine (540 mg, 1.5 mmol) in chloroform (7 mL) containing trifluoroacetic acid (1 mL) was allowed to stir at ambient temperature for 15-25 hours. The solvent was removed on a rotary evaporator, the residue dissolved in chloroform and washed with aq. Na2CO3. The dried (Na2SO4) chloroform extract was evaporated to give 4-(3-propyl-2-oxo-1-benzimidazolinyl)piperidine as an oil which was used as is.

Workup

  1. customThe solvent was removed on a rotary evaporator
  2. dissolutionthe residue dissolved in chloroform
  3. washwashed with aq. Na2CO3
  4. dry with materialThe dried (Na2SO4) chloroform
  5. extractionextract
  6. customwas evaporated

Sources & evidence

ORD record
ord-4ae5bc81940943cfad98de7258c50688
Source dataset
uspto-grants-2000_08
Patent number
US06096763

Reaction notes

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