Potassium Carbonate → 3-(4-Methylsulfonylpiperazin-1-yl)propan-1-ol

HRID 916381Notes

Reaction equation

HRID 916381 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].Br[CH2:12][CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 7091611-(Methylsulfonyl)piperazine

Product 1

HCID 219360993-(4-Methylsulfonylpiperazin-1-yl)propan-1-olYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 1-(methylsulfonyl)piperazine (3 g, 18.3 mmol), 3-bromopropan-1-ol (3.3 g, 23.8 mmol) and potassium carbonate (3.28 g, 23.8 mmol) in acetonitrile (20 ml) was stirred at 70° C. for 4 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 methanol and methylene chloride to give 3-(4-methylsulphonylpiperazin-1-yl)propan-1-ol (2.93 g, 72%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography
  5. washeluting
  6. temperaturewith increasingly polar mixtures of methanol and methylene chloride

Sources & evidence

ORD record
ord-c83af9f3c96f4ad4b58fc956617639da
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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