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

HRID 916404Notes

Reaction equation

HRID 916404 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-8730a1c7dd524f44ab85c58817f15384
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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