Cyclohexanone → HCID 21474190, compound

HRID 2294162Notes

Reaction equation

HRID 2294162 reaction equation
[Na].[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([N:11]3[C:15]4[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=4[N:13]=[CH:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[C:21]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CO>[C:21]1([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[C:7]([N:11]4[C:15]5[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=5[N:13]=[CH:12]4)[CH:6]=3)[NH:2][CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 5360545SodiumHCID 21474183HCID 21474183, compound

Product 1

HCID 21474190HCID 21474190, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of sodium (0.325 g, 14.2 mmol, 7.0 equivalents) in absolute methanol (10 mL) was added 1-(indol-5-yl)-5-methylbenzimidazole (0.500 g, 2.02 mmol) and cyclohexanone (0.84 mL, 8.08 mmol, 4.0 equivalents), and the resulting reaction solution was heated at reflux under nitrogen for 12 hours. The resulting mixture was evaporated under reduced pressure, and the residue was column chromatographed using silica gel (approximately 25 g) and eluted with 20% ethyl acetate in methylene chloride to afford the title compound (0.160 g, 0.49 mmol, 24%) as a pale yellow foam. Mp, 101.0°-102.0° C.; Rf =0.75 in 5% MeOH in methylene chloride; 1H NMR (CD3OD) d 8.25 (s, 1H), 7.88 (s, 1H), 7.53-7.50 (m, 2H), 7.35-7.33 (m, 2H), 7.21 (br d, J=8.5 Hz, 1H), 7.12 (d, J=8.2 Hz, 1Hz), 6.14 (br m, 1H), 4.90 (s, 1 exchangeable H), 2.46 (s, 3H), 2.19 (br m, 2H), 1.86-1.75 (m, 2H), 1.75-1.63 (m, 2H); IR (KBr) 2929, 2859, 1615, 1579, 1494, 1447 cm-1.

Workup

  1. customthe resulting reaction solution
  2. temperaturewas heated
  3. temperatureat reflux under nitrogen for 12 hours
  4. customThe resulting mixture was evaporated under reduced pressure
  5. customchromatographed
  6. washeluted with 20% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-8bc167b871f64b48bc0adca5ed22a299
Source dataset
uspto-grants-1997_11
Patent number
US05688809

Reaction notes

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