Trifluoroacetic acid water → 5-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

HRID 132587Notes

Reaction equation

HRID 132587 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:17]=3[NH:16][C:15]2=[O:24])[CH2:10][CH2:9]1)=O)(C)(C)C.O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]2[N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:15](=[O:24])[NH:16][C:17]=2[CH:22]=1

Participants

4

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 66652167tert-butyl 4-(5-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(5-chloro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (1.50 g, 4.3 mmol) and H2O/TFA 5% (15 mL) in CH2Cl2 (20 ml) was stirred at room temperature for 1 h, after which the solvent was removed in vacuo. The residue was purified by gradient flash chromatography on silica gel (CH2Cl2 to EtOH), yielding an off-white/pinkish solid (0.97 g, 90%).

Workup

  1. customafter which the solvent was removed in vacuo
  2. customThe residue was purified by gradient flash chromatography on silica gel (CH2Cl2 to EtOH)

Sources & evidence

ORD record
ord-b15cfeceb3f5479d88f6e9e8bede1813
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

Loading…