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

HRID 2068025Notes

Reaction equation

HRID 2068025 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-(methylsulphonyl)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-e8e5a1b267bf47aa83a725c1ed93fcaa
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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