1-Piperazinecarboxylic acid, ethyl ester → HCID 10912032, compound

HRID 1977125Notes

Reaction equation

HRID 1977125 reaction equation
Br[CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[N:13]1(C(OCC)=O)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C.[OH-].[Na+]>C(OCC)C.C(OCC)(=O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH:2]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH3:12])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 37882192-Bromo-1-(4-chlorophenyl)propan-1-one

Product 1

HCID 10912032HCID 10912032, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-4′-chloropropiophenone, (741 mg, 3 mmol); ethyl 1-piperazinecarboxylate (474 mg, 3 mmol); triethylamine (0.42 mL, 3 mmol) in diethyl ether (10 mL) was heated at reflux for 3 hours (reaction was monitored by Thin Layer Chromatography (TLC)). The reaction mixture was cooled and further diluted with ethyl acetate and washed with water, brine and dried over Na2SO4. After evaporation of the solvent in vacuo, the crude viscous liquid was treated with conc. HCl (15 mL) at refluxing temperature for 48 hrs. The cooled reaction mixture was made alkaline by addition of 50% NaOH and extracted with ethyl acetate. The combined extracts were washed with water, brine and dried over Na2SO4. After evaporation of the solvent 4′chloro-2-(piperazin-1-yl)propiophenone was obtained as a semisolid which was reacted without further purification.

Workup

  1. temperatureat reflux for 3 hours
  2. custom(reaction was monitored by Thin Layer Chromatography (TLC))
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation of the solvent in vacuo
  7. additionthe crude viscous liquid was treated with conc. HCl (15 mL)
  8. temperatureat refluxing temperature for 48 hrs
  9. customThe cooled reaction mixture
  10. extractionextracted with ethyl acetate
  11. washThe combined extracts were washed with water, brine
  12. dry with materialdried over Na2SO4
  13. customAfter evaporation of the solvent 4′chloro-2-(piperazin-1-yl)propiophenone
  14. customwas obtained as a semisolid which
  15. customwas reacted without further purification

Sources & evidence

ORD record
ord-261719b7e69b4635b2322a932889710c
Source dataset
uspto-grants-2001_05
Patent number
US06232314B1

Reaction notes

Loading…