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

HRID 2064181Notes

Reaction equation

HRID 2064181 reaction equation
[CH3:1][C:2]1[C:3]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[C:6]=2[CH:24]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[C:3]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 598501771,1-Dimethylethyl 4-{6-methyl-5-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate

Product 1

HCID 598501546-Methyl-5-[(1-methylethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 291.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-{6-methyl-5-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate (D76) (0.14 mmol, 53 mg) in dichloromethane (1 mL) was treated with trifluoroacetic acid (1 mL) under argon at room temperature and was allowed to stir for 1 h. The mixture was then concentrated under reduced pressure, the residue was treated with 10% aqueous sodium carbonate solution and extracted 3 times with ethyl acetate. The organics were combined, dried and concentrated under reduced pressure to give the title compound (118 mg, >>100%). M+H 290.3.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additionthe residue was treated with 10% aqueous sodium carbonate solution
  3. extractionextracted 3 times with ethyl acetate
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15d30fb7cbec4d8b93f53d90e3e6a454
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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