Hydrogen Bromide → HCID 21333176, compound

HRID 1390617Notes

Reaction equation

HRID 1390617 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14][N:13](C(OCC)=O)[CH2:12][CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].Br.[OH-].[Na+].Cl>C(O)C.O>[ClH:1].[Cl:9][C:6]1[CH:5]=[C:4]([N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric Acid3×HCID 14798Sodium HydroxideHCID 21333177HCID 21333177, compound

Product 1

HCID 21333176HCID 21333176, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(3,4,5-Trichlorophenyl)-4-ethoxycarbonylpiperazine (12.3g) was refluxed with 48% hydrobromic acid (100 ml) overnight. The reaction was cooled, water added followed by aqueous sodium hydroxide solution (600 ml; 10%). The product was extracted into ether (3 × 100 ml), the ether extracts combined, washed with water (3 × 100 ml) till neutral, dried (anh. Na2SO4) and evaporated giving a brown oil which soon solidified (10.14g). The free base was converted to the hydrochloride (9.42g) by dissolving in dry ethanol and adding ethereal HCl till the hydrochloride precipitated out.

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe product was extracted into ether (3 × 100 ml)
  3. washwashed with water (3 × 100 ml) till neutral,
  4. dry with materialdried (anh. Na2SO4)
  5. customevaporated
  6. customgiving a brown oil which
  7. customprecipitated out

Sources & evidence

ORD record
ord-ab5a2876b09840baa3f00bc05630fefa
Source dataset
uspto-grants-1979_02
Patent number
US04139621

Reaction notes

Loading…