Hydrochloric Acid → HCID 66582368, compound

HRID 1972374Notes

Reaction equation

HRID 1972374 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.C(Cl)[Cl:9].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[S:16](Cl)(=[O:18])=[O:17].Cl>O.O1CCOCC1.CCOC(C)=O>[ClH:9].[CH3:1][C@H:2]1[CH2:7][N:6]([S:16]([C:12]2[S:11][CH:15]=[CH:14][CH:13]=2)(=[O:18])=[O:17])[CH2:5][CH2:4][NH:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 855182-Thiophenesulfonyl chlorideHCID 27342192-Methylpiperazine, (S)-

Product 1

HCID 66582368HCID 66582368, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL round-bottomed flask was charged with (S)-2-methylpiperazine (10.23 g, 102 mmol, Sigma-Aldrich, St. Louis, Mo.) and 100 mL of CH2Cl2. After cooling to 0° C., 2-thiophenesulfonyl chloride (18.65 g, 102 mmol, Sigma-Aldrich, St. Louis, Mo.) was added. This mixture was stirred at 0° C. for 15 min then diluted with water (100 mL). The layers were separated and the organics were dried (MgSO4) and concentrated to give an oil. To this oil was added 300 mL of EtOAc and 28 mL of 4 M HCl in dioxane. The resulting white precipitate was collected by filtration to give (S)-2-methyl-4-(2-thiophenylsulfonyl)piperazine hydrochloride (26 g).

Workup

  1. customThe layers were separated
  2. dry with materialthe organics were dried (MgSO4)
  3. concentrationconcentrated
  4. customto give an oil
  5. filtrationThe resulting white precipitate was collected by filtration

Sources & evidence

ORD record
ord-d7ca7686067944f2af746d53fc79497a
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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