Trifluoroacetic acid → 5-Fluoro-6-methyl-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 2064141Notes

Reaction equation

HRID 2064141 reaction equation
[F:1][C:2]1[C:24]([CH3:25])=[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>[F:1][C:2]1[C:24]([CH3:25])=[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 51072045tert-butyl 4-(5-fluoro-6-methyl-2-oxo-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 598502105-Fluoro-6-methyl-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-(5-fluoro-6-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidine-carboxylate (D29) (0.68 mmol, 239 mg) in dichloromethane (5 mL) was treated under argon at room temperature with trifluoroacetic acid (1 mL) and allowed to stir for 1 h. The mixture was concentrated, treated with 10% Na2CO3 aqueous solution, extracted 3 times with ethyl acetate. Organics were combined, dried on MgSO4, and concentrated under vacuum to give the title compound (0.64 mmol, 160 mg, 94% yield). M+H=250.2.

Workup

  1. concentrationThe mixture was concentrated
  2. additiontreated with 10% Na2CO3 aqueous solution
  3. extractionextracted 3 times with ethyl acetate
  4. customdried on MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-77ea5375e0e84566a0c2859c1e962c55
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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