Hydrochloric Acid → 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole

HRID 2415863Notes

Reaction equation

HRID 2415863 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.Cl>O>[CH3:7][N:6]1[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=[C:2]1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazole

Product 1

HCID 6675511-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1 g (6.02 mmol) of 2-chloro-1-methyl-benzimidazole and 2.58 g (30 mmol) of piperazine is heated to 150° C. without a solvent. The cooled melt is combined successively with water and dilute hydrochloric acid and extracted with dichloromethane. Then the aqueous phase is made alkaline with dilute sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulphate and concentrated by evaporation. The product is purified by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia=5:1:0.1).

Workup

  1. extractionextracted with dichloromethane
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. customThe product is purified by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia=5:1:0.1)

Sources & evidence

ORD record
ord-2fa0de9281d94d13a7aafd0340a3f084
Source dataset
uspto-grants-2004_11
Patent number
US06821967B2

Reaction notes

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