Potassium Carbonate → 3-(4-Prop-2-YN-1-ylpiperazin-1-YL)propan-1-OL

HRID 2068124Notes

Reaction equation

HRID 2068124 reaction equation
OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[CH2:15]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:16]#[CH:17].C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][CH2:33][OH:34]>C(#N)C>[CH2:15]([N:18]1[CH2:23][CH2:22][N:21]([CH2:31][CH2:32][CH2:33][OH:34])[CH2:20][CH2:19]1)[C:16]#[CH:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 872383581-Prop-2-ynylpiperazine diTFA salt

Product 1

HCID 450998243-(4-Prop-2-YN-1-ylpiperazin-1-YL)propan-1-OLYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

1-Prop-2-yn-1-ylpiperazine diTFA salt (704 mg, 2 mmol), (prepared as described for the starting material in Example 26), was dissolved in acetonitrile (5 ml). Potassium carbonate (1.38 g, 10 mmol) and 3-bromopropan-1-ol (180 μL, 2 mmol) were added and the mixture heated to 85° C. for 6.5 hours. The reaction mixture was cooled, filtered and concentrated to give an oil. This was triturated with diethyl ether to give a white solid, which was partitioned between dichloromethane and water. The organic phase was then dried (MgSO4) and concentrated to give 3-(4-prop-2-yn-1-ylpiperazin-1-yl)propan-1-ol (286 mg, 79%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customto give an oil
  5. customThis was triturated with diethyl ether
  6. customto give a white solid, which
  7. customwas partitioned between dichloromethane and water
  8. dry with materialThe organic phase was then dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-77ff501408fc42b1b08b046dce3b3e15
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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