Hydrochloric Acid → 1-(2-Furoyl)piperazine

HRID 343272Notes

Reaction equation

HRID 343272 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 6N 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-82c6f48e8cf44601ac4c07201fdf6858
Source dataset
uspto-grants-1999_01
Patent number
US05861309

Reaction notes

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