Trifluoroacetic acid → 5-Chloro-6-[(1-methylethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 2064191Notes

Reaction equation

HRID 2064191 reaction equation
[Cl:1][C:2]1[C:24]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:23][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:24]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:23][C:5]2[N:6]([CH:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 598501801,1-Dimethylethyl 4-{5-chloro-6-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate

Product 1

HCID 598501865-Chloro-6-[(1-methylethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-{5-chloro-6-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate (D86, 140 mg, 0.34 mmol) in dichloromethane (3 ml) was treated with trifluoroacetic acid (3 ml) and stirred at room temperature under argon for 1 hr. The mixture was concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate (×3). The combined extract was dried (MgSO4) and concentrated under vacuum to leave the title compound as a red oil (94 mg, 83%). M++H=310.0.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue treated with 10% Na2CO3 solution
  3. extractionextracted with ethyl acetate (×3)
  4. extractionThe combined extract
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-43d69491286847848d4ecfc45730e814
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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