Triethylamine → 1-Methanesulfonyl-3,5-dimethylpiperazine

HRID 517722Notes

Reaction equation

HRID 517722 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][CH:7]1[CH2:12][NH:11][CH2:10][CH:9]([CH3:13])[NH:8]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:6][CH:7]1[NH:8][CH:9]([CH3:13])[CH2:10][N:11]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 660562,6-Dimethylpiperazine

Product 1

HCID 638725321-Methanesulfonyl-3,5-dimethylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (1.42 mL, 18.4 mmol) in DCM (10 mL) was added dropwise to a solution of 2,6-dimethylpiperazine (2 g, 17.5 mmol) and triethylamine (2.56 mL, 18.4 mmol) in DCM (10 mL) under nitrogen. The mixture was stirred for 30 min. The solvent was removed and the residue was applied to a 5 g aminopropyl SPE cartridge to give the product as a yellow solid (2.3 g), ˜10:1 mixture of cis and trans isomers by NMR.

Workup

  1. customThe solvent was removed
  2. customto give

Sources & evidence

ORD record
ord-bbc22bda9dca4f1b903910bfc88e3904
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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