Allyl bromide → 1-Allylpiperazine

HRID 1582271Notes

Reaction equation

HRID 1582271 reaction equation
F[C:2](F)(F)[C:3]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=O.[CH2:13](Br)C=C.C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH2:3]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[CH:2]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 7172020Trifluoroacetylpiperazine

Product 1

HCID 8064221-AllylpiperazineYield 155.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2,2,2-trifluoro-1-piperazin-1-yl-ethanone (515 mg, 2.83 mmol) in dry CH3CN (6 mL) was added allyl bromide (0.32 mL, 3.7 mmol) and powdered potassium carbonate (0.78 g, 5.65 mmol) and the mixture stirred overnight. The reaction was concentrated under reduced pressure, diluted with CH2Cl2 (30 mL) and water (30 mL) and the aqueous layer extracted with CH2Cl2 (2×20 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the crude di-protected piperazine (0.554 g) which was used without further purification in the next reaction.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additiondiluted with CH2Cl2 (30 mL) and water (30 mL)
  3. extractionthe aqueous layer extracted with CH2Cl2 (2×20 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af7f9b384cf8450fb69bbc6a0a4b482c
Source dataset
uspto-grants-2004_05
Patent number
US06734191B2

Reaction notes

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