1,2-Dichloroethane → {3-[4-(Ethylsulfonyl)piperazin-1-yl]-2-fluorophenyl}methanol

HRID 1021291Notes

Reaction equation

HRID 1021291 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([F:22])=[C:12]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.ClCCCl.[CH2:27]([S:29](Cl)(=[O:31])=[O:30])[CH3:28].C(Cl)(Cl)Cl>O>[CH2:27]([S:29]([N:19]1[CH2:18][CH2:17][N:16]([C:12]2[C:11]([F:22])=[C:10]([CH2:9][OH:8])[CH:15]=[CH:14][CH:13]=2)[CH2:21][CH2:20]1)(=[O:31])=[O:30])[CH3:28]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6212ChloroformHCID 11667Ethanesulfonyl chlorideHCID 866862021-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]piperazine

Product 1

HCID 68310253{3-[4-(Ethylsulfonyl)piperazin-1-yl]-2-fluorophenyl}methanolYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]piperazine (140 mg) was mixed with DCE (4 ml), and ethanesulfonyl chloride (122 mg) and TEA (145 mg) were added thereto, followed by stirring at room temperature for 2 hours. CHCl3 and water were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was mixed with THF (4 ml), and a 1 M TBAF/THF solution (0.9 ml) was added thereto, followed by stirring at room temperature for 2 hours. EtOAc and water were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain {3-[4-(ethylsulfonyl)piperazin-1-yl]-2-fluorophenyl}methanol (123.9 mg).

Workup

  1. additionwere added
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. additionThe obtained residue was mixed with THF (4 ml)
  5. additiona 1 M TBAF/THF solution (0.9 ml) was added
  6. stirringby stirring at room temperature for 2 hours
  7. additionEtOAc and water were added to the reaction mixture
  8. dry with materialthe organic layer was dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-1a1dc289460e47c1866b9db05c90f0ce
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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