Piperazine → Ammonia

HRID 476566Notes

Reaction equation

HRID 476566 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[O:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1>C(O)C>[NH3:1].[O:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 119862-Chlorobenzoxazole

Product 2

HCID 222AmmoniaHCID 6478182-(Piperazin-1-yl)-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of piperazine (8 g, 93 mmole) in ethanol (30 ml) was added 2-chlorobenzoxazole (3 g, 19.5 mmole) dropwise. The resulting reaction was exothermic. The mixture was then stirred for 18 hours at room temperature, quenched by the addition of methylene chloride (50 ml) and the resulting precipitate removed by filtration. The filtrate was concentrated under reduced pressure then purified by flash column chromatography on silica gel eluting with methylene chloride: methanol: 0.88 ammonia solution (90:10:1) to yield the title compound, m.p. 70°-72° (1.8 g, 46%), which was used directly.

Workup

  1. customThe resulting reaction
  2. customquenched by the addition of methylene chloride (50 ml)
  3. customthe resulting precipitate removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthen purified by flash column chromatography on silica gel eluting with methylene chloride

Sources & evidence

ORD record
ord-0f46eb497d1e4b0d92da8198fd4c23c4
Source dataset
uspto-grants-1989_12
Patent number
US04885294

Reaction notes

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