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

HRID 2068048Notes

Reaction equation

HRID 2068048 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(OCC)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

6

Reactant 3

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

Product 1

HCID 114467711-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-oneYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

1-Acetylpiperazine (15.0 g, 117 mmol) was dissolved in acetonitrile (200 ml) and potassium carbonate (40.4 g, 293 mmol) was added followed by 3-bromo-1-propanol (10.6 ml, 117 mmol). The mixture was heated at reflux for 2.5 hours, cooled, filtered and concentrated under reduced pressure. The resulting viscous oil was cooled in ice for 3 hours and the crystalline product that formed was suspended in diethyl ether and filtered off. The hydroscopic solid was dried under vacuum (P2O5) overnight to give 3-(4-acetylpiperazin-1-yl)propan-1-ol (17.3 g, 90%) as a pale yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. temperatureThe resulting viscous oil was cooled in ice for 3 hours
  7. customthe crystalline product that formed
  8. filtrationfiltered off
  9. dry with materialThe hydroscopic solid was dried under vacuum (P2O5) overnight

Sources & evidence

ORD record
ord-3a3f212492f745749b3344bedb77a229
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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