1-Phenylpiperazine → HCID 15053393, compound

HRID 1032158Notes

Reaction equation

HRID 1032158 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1.[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.O>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]([N:25]3[CH2:26][CH2:27][N:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:23][CH2:24]3)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70961-PhenylpiperazineHCID 15053366HCID 15053366, compound

Product 1

HCID 15053393HCID 15053393, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.9 g (0.01 mole) of 3-(4-bromophenoxy)-1-azetidinecarbonyl chloride in 15 ml of tetrahydrofuran was treated while stirring with 1.6 g (0.01 mole) of 1-phenylpiperazine added all at once, a solid formed instantaneously and after stirring for 2 hr, the reaction mixture was diluted with 200 ml of water, the solid did not dissolve. The solid was removed by filtration and when triturated with chloroform, all but about 1 g of solid dissolved. The chloroform solution was dried over magnesium sulfate then concentrated in vacuo. The oily residue crystallized when triturated with ligroin. Recrystallization from benzene/ligroin yielded 2.0 g (48.1%) of fine white crystals, m.p. 160°-161° C.

Workup

  1. additionadded all at once, a solid
  2. customformed instantaneously
  3. dissolutionthe solid did not dissolve
  4. customThe solid was removed by filtration and when
  5. customtriturated with chloroform
  6. dissolutionall but about 1 g of solid dissolved
  7. dry with materialThe chloroform solution was dried over magnesium sulfate
  8. concentrationthen concentrated in vacuo
  9. customThe oily residue crystallized when
  10. customtriturated with ligroin
  11. customRecrystallization from benzene/ligroin

Sources & evidence

ORD record
ord-7ab40cba49b14e64a87f097534e198ac
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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