Water → 2-(Piperazin-1-yl)-1,3-benzoxazole

HRID 1267268Notes

Reaction equation

HRID 1267268 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:15]1[O:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1.O>C(Cl)Cl>[N:1]1([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 8471TriethylamineHCID 119862-Chlorobenzoxazole

Product 1

HCID 6478182-(Piperazin-1-yl)-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous piperazine (5.6 g) was dissolved in methylene chloride (100 ml) to which was subsequently added triethylamine (4.5 ml). With cooling in an ice bath, to this was added dropwise 2-chlorobenzoxazole (3.7 ml) in small portions, followed by 45 minutes of stirring. The reaction solution was mixed with water, extracted with methylene chloride and then washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order. The organic layer was dried with magnesium sulfate and the solvent was evaporated under a reduced pressure. Thereafter, the thus obtained mixture was purified by a silica gel column chromatography (methanol) to obtain the title compound 2-(1-piperazinyl)benzoxazole,(4.751 g) in the form of yellow crystalline powder.

Workup

  1. temperatureWith cooling in an ice bath
  2. extractionextracted with methylene chloride
  3. washwashed with saturated sodium bicarbonate aqueous solution and saturated brine in that order
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customThereafter, the thus obtained mixture was purified by a silica gel column chromatography (methanol)

Sources & evidence

ORD record
ord-a7fb778b44024608adc12e60afb061e1
Source dataset
uspto-grants-2003_04
Patent number
US06552057B2

Reaction notes

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