Triethylamine → 1-(Methylsulfonyl)-4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine

HRID 1723826Notes

Reaction equation

HRID 1723826 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:1])([F:17])[F:18])=[CH:10][CH:9]=2)[CH2:12][CH2:13]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 435103441-[4-(2,2,2-Trifluoroethoxy)phenyl]piperazine

Product 1

HCID 210686241-(Methylsulfonyl)-4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazineYield 19.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine (13.48 g, 50 mmol) was dissolved in DCM (500 mL) and cooled to 0° C. Triethylamine (29 mL, 0.2 mol) was added, followed by the dropwise addition of methanesulfonyl chloride (4.2 mL, 55 mmol). The reaction was then allowed to warm to room temperature and stir overnight, before being quenched by the addition of water. The layers were separated, and the organic phase dried (MgSO4), filtered and concentrated. The residue was recrystallised from hot ethanol to give pure 1-(methylsulfonyl)-4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine (3.3 g, 18%).

Workup

  1. temperatureto warm to room temperature
  2. custombefore being quenched by the addition of water
  3. customThe layers were separated
  4. dry with materialthe organic phase dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallised from hot ethanol

Sources & evidence

ORD record
ord-0c7223e91e814e678a6c46b4b906b5a2
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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