Cyclohexene oxide → HCID 57057280, compound

HRID 1677843Notes

Reaction equation

HRID 1677843 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH:10]12[O:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]2>O>[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH:5]1[C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[OH:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 9246Cyclohexene oxideHCID 837951-Acetylpiperazine

Product 1

HCID 57057280HCID 57057280, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-acetylpiperazine (5 g, 39 mmol) and cyclohexene oxide (3.95 mL, 39 mmol) in water (1.2 mL) was refluxed for 16 hours. The cooled reaction mixture was partitioned between 40% NaOH aqueous solution (20 mL) and diethyl ether (2×20 mL). The combined organic layers were dried over sodium sulfate and the solvent was evaporated in vacuo to yield 7.63 g of the title compound as white crystals (87% yield)

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe cooled reaction mixture
  3. customwas partitioned between 40% NaOH aqueous solution (20 mL) and diethyl ether (2×20 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7bf4f785f0c74622a578ba27013ef922
Source dataset
uspto-grants-2011_08
Patent number
US08008342B2

Reaction notes

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