Succinic Acid → HCID 17906612, compound

HRID 858338Notes

Reaction equation

HRID 858338 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[CH2:15][C:16]([O-:18])=[O:17].C(O)(=O)CCC(O)=O>C(O)(C)C>[CH2:2]([O:18][C:16](=[O:17])[CH3:15])[CH3:3].[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1110Succinic AcidHCID 4837PiperazineHCID 8471TriethylamineHCID 518964Chloroacetate

Product 1

HCID 17906612HCID 17906612, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent3×

Procedure

To a reaction blend containing 100 g (3 Eq, 0.515 mol, MW=194) of piperazine, 26.3 mL (1.1 Eq, 0.189 mol, MW=101, d=0.726) of triethylamine in 200 mL of isopropanol, add to a solution previously prepared of 18.4 mL (1 Eq., 0.172 mol, MW=122.55, d=1.15) of chloroacetate of ethyl in 140 mL of isopropanol under stirring, at room temperature. Keep the reaction medium under stirring, monitoring the reaction termination by means of a chromatography of the thin layer (about 2–3 hours). Add a solution of 40.6 g (0.344 mol) of succinic acid in 140 mL of isopropanol. Keep the system under stirring for about 30 minutes to assure total precipitation of the succinate salt of piperazine formed. Filter this salt and concentrate the filtrate containing the mono and dialkyled derivatives. We obtain a slightly yellowish oil, which is used in later phases without purification.

Workup

  1. additionadd to a solution
  2. stirringunder stirring
  3. customby means of a chromatography of the thin layer (about 2–3 hours)
  4. stirringunder stirring for about 30 minutes
  5. customprecipitation of the succinate salt of piperazine
  6. customformed
  7. filtrationFilter this salt
  8. concentrationconcentrate the filtrate
  9. additioncontaining the mono and
  10. customWe obtain a slightly yellowish oil, which
  11. customis used in later phases without purification

Sources & evidence

ORD record
ord-949d5b29ef44405d8f8d03eb0244e8df
Source dataset
uspto-grants-2006_12
Patent number
US07148350B2

Reaction notes

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