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

HRID 2068013Notes

Reaction equation

HRID 2068013 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-179c834f9c8e4a77aac4bdf3b0e19d01
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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