Diethyl Ether → 4-Piperidino-5,7-dinitro-2-trifluoromethylbenzimidazole

HRID 1974345Notes

Reaction equation

HRID 1974345 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:17]2[NH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[N:14][C:13]=2[C:12]([N+:22]([O-:24])=[O:23])=[CH:11][C:10]=1[N+:25]([O-:27])=[O:26].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.CCOCC>C1C=CC=CC=1>[N:28]1([C:9]2[C:17]3[NH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[N:14][C:13]=3[C:12]([N+:22]([O-:24])=[O:23])=[CH:11][C:10]=2[N+:25]([O-:27])=[O:26])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8082PiperidineHCID 8471TriethylamineHCID 1356775774-Chloro-5,7-dinitro-2-trifluoromethylbenzimidazole

Product 1

HCID 214893574-Piperidino-5,7-dinitro-2-trifluoromethylbenzimidazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Triethylamine (1.0 gram; 0.00968 mole) was added to 3.0 grams of 4-chloro-5,7-dinitro-2-trifluoromethylbenzimidazole (0.00968 mole) in 200 milliliters of benzene. There was then added dropwise 0.8 gram of piperidine (0.00968 mole) in 10 milliliters of benzene. The resulting reaction mixture was refluxed overnight, cooled, an amount of ether added, and the mixture filtered. The filtrate was evaporated, yielding the desired 4-piperidino-5,7-dinitro-2-trifluoromethylbenzimidazole product as an orange solid. It was recrystallized from benzene as a light brown solid, m.p., 199°-206° C. NMR analysis confirmed the identity but suggested the presence of a small amount of triethylamine.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. temperaturecooled
  4. filtrationthe mixture filtered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-be9073c9e7ab4bdb88a52d8dc1733f8b
Source dataset
uspto-grants-1976_12
Patent number
US04000295

Reaction notes

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