Piperidine → HCID 135834136, compound

HRID 1017723Notes

Reaction equation

HRID 1017723 reaction equation
[Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:23]=O)=[C:13]([NH:15][C:16](=[O:22])OC(C)(C)C)[CH:14]=1)(C(C)(C)C)(C)C.[NH:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[CH2:34]C(OCC)=O.N1CCCCC1.F.F.F.C(N(CC)CC)C>C(O)C.C(#N)C>[NH:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[C:34]1[C:16](=[O:22])[NH:15][C:13]2[C:12]([CH:23]=1)=[CH:11][CH:10]=[C:9]([OH:8])[CH:14]=2

Participants

7

Reactant 4

HCID 8082PiperidineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 11163965HCID 11163965, compound

Product 1

HCID 135834136HCID 135834136, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl 5-{[tert-butyl(dimethyl)silyl]oxy}-2-formylphenylcarbamate (12-4, 0.57 g, 2.4 mmol, 1 equiv), ethyl 1H-benzimidazol-2-ylacetate (0.50 g, 2.4 mmol, 1.0 equiv, prepared by the method of Rahmouni, M, Derdour, A., Bazureau, J., and Hamelin Tetrahedron Lett. 1994, 35, 4563-4564), and piperidine (0.12 mL, 1.2 mmol, 0.5 equiv) in ethanol (50 mL) was heated at reflux for 20 h. The reaction mixture was cooled and concentrated. A solution of the residue and triethylamine trihydrofluoride (0.38 mL, 2.3 mmol, 0.97 equiv) in acetonitrile (30 mL) was stirred at 30° C. for 2.5 h. The precipitate which formed was filtered and air dried to give 3-(1H-benzimidazol-2-yl)-7-hydroxy-2(1H)-quinolinone (12-5) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.51 (s, 1H), 12.19 (s, 1H), 10.45 (br s, 1H), 8.95 (s, 1H), 7.76 (d, 1H, J=8.8 Hz), 7.68 (m, 1H), 7.59 (m, 1H), 7.18 (m, 2H), 6.82 (s, 1H), 6.75 (d, 1H, J=8.8 Hz).

Workup

  1. temperatureat reflux for 20 h
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customThe precipitate which formed
  5. filtrationwas filtered
  6. customair dried

Sources & evidence

ORD record
ord-0e164d3e8fca404285c218c9101d2a47
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

Loading…