Pyridine → 1-(4-Fluorophenyl)-4-(methylsulfonyl)piperazine

HRID 1392135Notes

Reaction equation

HRID 1392135 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:21]([CH3:20])(=[O:23])=[O:22])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 752601-(4-Fluorophenyl)piperazine

Product 1

HCID 6690391-(4-Fluorophenyl)-4-(methylsulfonyl)piperazineYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-fluorophenyl)piperazine (35 g, 194 mmol) and pyridine (17.5 ml) in dry dichloromethane (200 ml) at 0° C. was added methanesulfonyl chloride (20 ml , 258 mmol) dropwise. The mixture was stirred for 3 hours at room temperature. The mixture was washed with water and extracted with dichloromethane (2×100 ml). The organic layers were dried with MgSO4 and evaporated in vacuo. The residue was triturated and washed with methanol to give 1-(4-fluorophenyl)-4-(methanesulfonyl)piperazine (39.35 g) as white crystals.

Workup

  1. washThe mixture was washed with water
  2. extractionextracted with dichloromethane (2×100 ml)
  3. dry with materialThe organic layers were dried with MgSO4
  4. customevaporated in vacuo
  5. customThe residue was triturated
  6. washwashed with methanol

Sources & evidence

ORD record
ord-060f8a7974be43fcb265646de16f376d
Source dataset
uspto-grants-2008_03
Patent number
US07342020B2

Reaction notes

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