Triethylamine → 1-(Methanesulfonyl)-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine

HRID 1723818Notes

Reaction equation

HRID 1723818 reaction equation
[F:1][C:2]([F:19])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:27][S:28]([N:16]1[CH2:17][CH2:18][N:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][C:2]([F:1])([F:19])[CH:3]([F:4])[F:5])=[CH:8][CH:9]=2)[CH2:14][CH2:15]1)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 544321851-[4-(1,1,2,2-Tetrafluoroethoxy)phenyl]piperazine

Product 1

HCID 575592431-(Methanesulfonyl)-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine (10.95 g, 0.04) was dissolved in DCM (500 ml) and triethylamine (18.5 ml, 0.13 mol) was added. The mixture was cooled to 0° C. and methane sulphonyl chloride (7.4 ml, 0.048 mol) added. Allowed to reach ambient temperature and stirred overnight. The reaction mixture washed with water and the organic phase collected, dried over MgSO4, filtered and evaporated to dryness. The residual solid was crystallised from ethanol to yield 1-(methylsulfonyl)-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine as a white solid. Yield 12.3 g (78.5%)

Workup

  1. customto reach ambient temperature
  2. washThe reaction mixture washed with water
  3. customthe organic phase collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residual solid was crystallised from ethanol

Sources & evidence

ORD record
ord-567157359b2e4428806073c2e10b9788
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

Loading…