Water → HCID 86614579, compound

HRID 1723821Notes

Reaction equation

HRID 1723821 reaction equation
[F:1][C:2]([F:31])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([CH2:22][CH:23]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)O)(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].C(N(CC)CC)C.CS(Cl)(=O)=O.O>C(Cl)Cl>[F:31][C:2]([F:1])([O:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([S:19](/[CH:22]=[CH:23]/[CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)(=[O:20])=[O:21])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1)[CH:3]([F:4])[F:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86614578HCID 86614578, compound

Product 1

HCID 86614579HCID 86614579, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-({4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazin-1-yl}sulfonyl)-1-(tetrahydro-2H-pyran-4-yl)ethanol (3.6 g, 0.008M) was dissolved in DCM (100 ml) and triethylamine (5.58 ml, 0.04 mol) was added. The mixture was cooled to 0° C. and methane sulphonyl chloride (0.94 ml, 0.012M) added with stirring at room temperature overnight. Water was added and the organic phase separated off, dried over MgSO4, filtered and evaporated to dryness to yield 1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-{[(E)-2-(tetrahydro-2H-pyran-4-yl)vinyl]sulfonyl}piperazine. Yield (3.15 g, 86.6%).

Workup

  1. customthe organic phase separated off
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-bc933ea5feec4856ba78669217e46fcf
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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