Hydrochloric Acid → 1-(2-Furoyl)piperazine

HRID 2287300Notes

Reaction equation

HRID 2287300 reaction equation
O.O.O.O.O.O.[NH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Cl.[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](Cl)=[O:20].[OH-].[Na+]>O>[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19]([N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 682422-Furancarbonyl chlorideHCID 120181Piperazine, hexahydrate

Product 1

HCID 5502061-(2-Furoyl)piperazineYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound and its preparation has been described in Great Britain Patents 1,390,014 and 1,390,015. Piperazine hexahydrate (194 g, 1 mole) was dissolved in 250 ml H2O. The solution was acidified to pH 4.5 with 6 N HCl. Furoyl chloride (130.5 g, 1 mole, Aldrich) was added along with 10% NaOH solution at such a rate that the pH was maintained at 4.5. After 1 hour, the solution was made basic (pH=8.5) with NaOH solution. The reaction mixture was continuously extracted with chloroform for 36 hours. The CHCl3 extract was dried over MgSO4, and filtered. Distillation gave 108.2 g product (60%), b.p. 132°-138° C./0.6 mm Hg, m.p. 69°-70° C.

Workup

  1. customThis compound and its preparation
  2. temperaturewas maintained at 4.5
  3. extractionThe reaction mixture was continuously extracted with chloroform for 36 hours
  4. extractionThe CHCl3 extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. distillationDistillation

Sources & evidence

ORD record
ord-3e710bbd9e1f435f9b67daf1c7465777
Source dataset
uspto-grants-2000_07
Patent number
US06083705

Reaction notes

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