Potassium Carbonate → 1-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-one

HRID 916368Notes

Reaction equation

HRID 916368 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][OH:20]>C(#N)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 837951-Acetylpiperazine

Product 1

HCID 114467711-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-oneYield 56.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-acetylpiperazine (3.85 g, 30 mmol), potassium carbonate (8.3 g, 60 mmol) and 3-bromo-1-propanol (4 ml, 45 mmol) in acetonitrile (30 ml) was heated and stirred at 80° C. for 5 hours. After cooling, the mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography, eluting with increasingly polar mixtures of methylene chloride and ethanol. The fractions containing the expected product were combined and evaporated to give 3-(4-acetylpiperazin-1-yl)propan-1-ol (3.15 g, 56%).

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography
  6. washeluting
  7. temperaturewith increasingly polar mixtures of methylene chloride and ethanol
  8. additionThe fractions containing the expected product
  9. customevaporated

Sources & evidence

ORD record
ord-66d4dbe04c264934894ebcaf08bb11e8
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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