Tetrahydrofuran → HCID 20201642, compound

HRID 979049Notes

Reaction equation

HRID 979049 reaction equation
O1CCCC1.[CH:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7].[CH3:14][N:15]([C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[C:16](Cl)=[O:17]>C(N(CC)CC)C>[CH:6]([N:8]1[CH2:13][CH2:12][N:11]([C:16](=[O:17])[N:15]([CH3:14])[C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:10][CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 821911-PiperazinecarboxaldehydeHCID 11062732HCID 11062732, compound

Product 1

HCID 20201642HCID 20201642, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into 600 ml of tetrahydrofuran, were dissolved 41 g of 1-formylpiperazine and 54.5 g of triethylamine. To the solution, while being stirred and cooled in ice, was added dropwise 56 g of 2,4,4-trimethylallophanyl chloride. The mixture was allowed to react at room temperature for 6 hours and the precipitate was removed by filtration. The filtrate was concentrated and the residue was recrystallized from tetrahydrofuran to obtain 41 g of 1-formyl-4-(2,4,4-trimethylallophanoyl)piperazine. This compound was mixed with 800 ml of 6N hydrochloric acid and the mixture was heated with stirring at 60° C. for one hour. The reaction mixture was concentrated and the residue was recrystallized from ethanol to obtain 35.2 g of 1-(2,4,4-trimethylallophanoyl)piperazine hydrochloride having a melting point of 215° C.

Workup

  1. temperaturecooled in ice
  2. customto react at room temperature for 6 hours
  3. customthe precipitate was removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customthe residue was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-3ea879f65a1147f0a895e0e711a967d8
Source dataset
uspto-grants-1987_05
Patent number
US04666911

Reaction notes

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