1-Bromo-3-chloropropane → 1-Acetyl-4-(3-chloropropoxy)piperazine

HRID 916408Notes

Reaction equation

HRID 916408 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[CH2:11][CH2:12][CH2:13][Cl:14].C(=O)([O-])[O-:16].[K+].[K+]>C(#N)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([O:16][CH2:11][CH2:12][CH2:13][Cl:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 837951-Acetylpiperazine

Product 1

HCID 666465241-Acetyl-4-(3-chloropropoxy)piperazineYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-acetylpiperazine (11.0 g, 7.8 mmol), 1-bromo-3-chloropropane (772 μl, 7.8 mmol) and potassium carbonate (2.7 g, 19.5 mmol) in acetonitrile (150 ml) was heated at reflux for 2 hours. The mixture was cooled, filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluting with methylene chloride/methanol (98/2) to give 1-acetyl-4-(3-chloropropoxy)piperazine (656 mg, 41%) as a colourless oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloride/methanol (98/2)

Sources & evidence

ORD record
ord-3625005acd6347a7b96862fce165e5e9
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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