Hydrochloric Acid → HCID 66655408, compound

HRID 517720Notes

Reaction equation

HRID 517720 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[OH-].[Na+].[S:10](Cl)([CH3:13])(=[O:12])=[O:11].Cl>C1COCC1>[CH3:1][C@H:2]1[NH:3][CH2:4][CH2:5][N:6]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 66655408HCID 66655408, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (2R)-2-methylpiperazine (1.00 g, 9.98 mmol) in NaOH (2 M aqueous, 10.5 ml, 21.0 mmol) and THF (15 ml) at 0° C. was added a solution of mesyl chloride (0.817 ml, 10.5 mmol) in THF (5 ml) over 30 seconds. The clear solution was stirred at 0° C. for 2 h. The reaction was poured into 2M aqueous HCl (20 ml), then the mixture washed with EtOAc (2×25 ml). The aqueous was adjusted to pH 12 with solid NaOH (˜1.5 g), then extracted with DCM (2×25 ml). The combined organics were passed through a phase separator and concentrated under vacuum to leave a white solid, (3R)-3-methyl-1-(methylsulfonyl)piperazine (352 mg).

Workup

  1. washthe mixture washed with EtOAc (2×25 ml)
  2. extractionextracted with DCM (2×25 ml)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e64dbc4cb0ee482797d07078023daf2a
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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