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

HRID 2180151Notes

Reaction equation

HRID 2180151 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 91.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 1-methylsulfonylpiperazine (1.58 g, 9.6 mmol), 3-bromo-1-propanol (1.13 ml, 12 mmol) and potassium carbonate (1.73 g, 12 mmol) in acetonitrile (10 ml) was stirred at 40° C. for 4 hours followed by 2 hours at 70° C. The mixture was cooled, filtered and the filtrate was evaporated under vacuum. The residue was purified by column chromatography eluting with methylene chloride/methanol (97/3 followed by 95/5) to give 3-(4-methylsulfonylpiperazin-1-yl)propan-1-ol (1.95 g, 91%).

Workup

  1. waitfollowed by 2 hours at 70° C
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated under vacuum
  5. customThe residue was purified by column chromatography
  6. washeluting with methylene chloride/methanol (97/3 followed by 95/5)

Sources & evidence

ORD record
ord-3633b1dca91345179491f9e6e1c25c08
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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