Piperazine → HCID 22665942, compound

HRID 1018416Notes

Reaction equation

HRID 1018416 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.C(C1OC1)Cl.[OH-].[Na+]>[Pt].O>[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 7835Epichlorohydrin2×HCID 8083MorpholineHCID 14798Sodium Hydroxide2×

Product 1

HCID 22665942HCID 22665942, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent3×

Conditions

Temperature
60 °C

Procedure

Into a round bottom flask equipped with stirrer, thermometer, dropping funnel and reflux condenser were weighed 154.8 g (1.8 mole) of piperazine and 69.6 g (0.8 mole) of morpholine and 220 ml of water. After a clear solution at 40° C. was obtained, the solution was heated to 55-65° C. and with vigorous stirring 185 g (2 mole) of epichlorohydrin were added at such a rate, that the temperature did not exceed 80° C. After all the epichlorohydrin had been added the reaction mixture was heated to 85° C. until all of the alkylating agents had been consumed (negative Preussmann test after 4 hours). 108.8 g (0.68 mole) of 25% NaOH and 40 g of water were added and the reaction mixture was stirred for another hour at 85° C. Then additional 47 g of water were added and the mixture was allowed to cool to room temperature. 233.6 g (equivalent to 1,292 mole oxidizable nitrogen atoms) were mixed with 22.1 g (0.276) of 50% NaOH and then heated to 55-65° C. At that temperature 102.4 g (1,421 mole) of H202 (47.2%) were added dropwise over a period of 3.5 hours. After the addition was completed, the reaction mixture was heated held at the same temperature for 3 more hours and was then stirred at room temperature overnight. Pt/C was added, unreacted H202 destroyed and the solution then filtered.

Workup

  1. customInto a round bottom flask equipped with stirrer
  2. temperaturereflux condenser
  3. customAfter a clear solution at 40° C. was obtained
  4. additionwere added at such a rate
  5. customdid not exceed 80° C
  6. temperaturewas heated to 85° C. until all of the alkylating agents
  7. customhad been consumed (negative Preussmann test after 4 hours)
  8. temperatureto cool to room temperature
  9. temperatureheated to 55-65° C
  10. additionAt that temperature 102.4 g (1,421 mole) of H202 (47.2%) were added dropwise over a period of 3.5 hours
  11. additionAfter the addition
  12. temperaturethe reaction mixture was heated
  13. stirringwas then stirred at room temperature overnight
  14. customunreacted H202 destroyed
  15. filtrationthe solution then filtered

Sources & evidence

ORD record
ord-5180818ccb484d458632930f4174c94b
Source dataset
uspto-grants-2002_11
Patent number
US06482787B1

Reaction notes

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