Piperazine → 1-(Tetrahydro-2-furoyl)piperazine

HRID 428358Notes

Reaction equation

HRID 428358 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([OH:8])=O.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C[Si](C)(C)N[Si](C)(C)C>C(Cl)(Cl)Cl>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:8]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 13838HexamethyldisilazaneHCID 86079(+-)-Tetrahydro-2-furoic acid

Product 1

HCID 27346411-(Tetrahydro-2-furoyl)piperazineYield 92.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

In a 100 ml round-bottom flask, tetrahydrofuran-2-carboxylic acid (3.48 grams, 30 mmole), piperazine (5.16 grams, 60 mmole) and 1,1,1,3,3,3-hexamethyldisilazane (4.83 grams, 30 mmole) were added, stirred under a nitrogen atmosphere and heated to 110° C. After 5 hours, the completion of the reaction was detected by thin-layer chromatography (TLC). After cooling to room temperature, the product was dissolved in chloroform, washed with a sodium hydrogen carbonate solution once and with water once. The organic layer was dried with anhydrous sodium sulfate, filtered, and applied suction to obtain 5.13 grams of Compound 3.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with a sodium hydrogen carbonate solution once
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-7610e8ede4d64082bff670d2cb85dabc
Source dataset
uspto-grants-2001_11
Patent number
US06313293B1

Reaction notes

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