Triethylamine → 1-Benzyl-4-methanesulfonyl-piperazine

HRID 2180149Notes

Reaction equation

HRID 2180149 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:6]([N:13]1[CH2:18][CH2:17][N:16]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:15][CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 759941-Benzylpiperazine

Product 1

HCID 7795071-Benzyl-4-methanesulfonyl-piperazineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (966 μl, 12.5 mmol) was added dropwise to a solution of 1-benzylpiperazine (2 g, 11.3 mmol) and triethylamine (1.74 ml, 12.5 mmol) in dry methylene chloride (30 ml) cooled at 0° C. After stirring for 1 hour at ambient temperature, the mixture was partitioned between water and methylene chloride. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with methylene chloride/ethyl acetate (7/3) to give 1-benzyl-4-methylsulfonylpiperazine (2.5 g, 87%).

Workup

  1. customthe mixture was partitioned between water and methylene chloride
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloride/ethyl acetate (7/3)

Sources & evidence

ORD record
ord-63ffe40b2ae245858f21d1027a494628
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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