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

HRID 2064079Notes

Reaction equation

HRID 2064079 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[C:9]=2[CH:27]=1)[CH3:3].FC(F)(F)C(O)=O>ClCCl>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[C:9]=2[CH:27]=1)[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574239181,1-Dimethylethyl 4-{6-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate

Product 1

HCID 574239196-[(1-Methylethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-{6-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate (D49, 351 mg, 0.93 mmol) in dichloromethane (5 ml) was treated with trifluoroacetic acid (3 ml) and stirred 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 concentrated under vacuum to leave the title compound as an orange oil (229 mg, 89%). M++H=276.1.

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. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-3b3b3fc8cd994b4da34ff98fc9782191
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

Loading…