Ethanol → 1-(Methylsulfonyl)piperazine

HRID 2357632Notes

Reaction equation

HRID 2357632 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7][CH2:6]1)(=[O:4])=[O:3].C(O)C.[H][H]>[Pd]>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 68455621HCID 68455621, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 7091611-(Methylsulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

Benzyl 1-piperazinecarboxylate (2.03 g, 9.22 mmol) was dissolved in pyridine (23.0 mL, 9.22 mmol) and cooled to 0° C. before methanesulfonyl chloride (2.85 mL, 36.9 mmol) was added. The reaction mixture was stirred at 0° C. for 30 minutes and warmed to RT for 2 h. The reaction mixture was diluted with 75 mL of ethyl acetate, added to a separation funnel, partitioned with 3 N HCl (aqueous), washed 3× with 50 mL of 3 N HCl (aqueous), and separated, before the aqueous layer was extracted 3× with chloroform/isopropanol, then dried over sodium sulfate, and concentrated in vacuo to give the title compound. Benzyl 4-(methylsulfonyl)piperazine-1-carboxylate (2.80 g, 9.4 mmol) was dissolved in ethanol (0.43 g, 9.4 mmol) before palladium, 10 wt. % on activated carbon (2.0 g) was added and a hydrogen balloon attached. The reaction mixture was stirred at RT for 2 h before it was filtered through a pad of Celite®, washed with methanol, and concentrated in vacuo to give the title compound. MS (ES+): 165 (M+H)+.

Workup

  1. additionwas added
  2. filtrationwas filtered through a pad of Celite®
  3. washwashed with methanol
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a76fd9f5b724ee0bbea9873e64a162a
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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