Triethylamine → 1-Methanesulfonyl-3,3-dimethylpiperazine

HRID 2403399Notes

Reaction equation

HRID 2403399 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([N:6]1[CH2:5][CH2:4][NH:3][C:2]([CH3:8])([CH3:1])[CH2:7]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 146641862,2-Dimethylpiperazine

Product 1

HCID 198151421-Methanesulfonyl-3,3-dimethylpiperazineYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2-dimethylpiperazine (400 mg) and triethylamine (0.59 mL) in dichloromethane (10 mL) at 0° C. was added dropwise methanesulfonyl chloride (0.30 mL). The reaction mixture was stirred at room temperature for 16 h and then quenched with water (10 mL) and extracted into dichloromethane (2×20 mL). The combined organic layers were washed with saturated aqueous brine solution (2×20 mL), dried (MgSO4) and concentrated to afford 1-methanesulfonyl-3,3-dimethyl-piperazine as a white solid (412 mg, 61%).

Workup

  1. customquenched with water (10 mL)
  2. extractionextracted into dichloromethane (2×20 mL)
  3. washThe combined organic layers were washed with saturated aqueous brine solution (2×20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7ea7b6a19e6f4b449fea1eb6b965ae59
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

Loading…