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Thionyl Chloride → 3-(2-(4-(4-(Trifluoromethoxy)phenoxy)piperidin-1-yl)ethoxy)propionyl chloride

HRID 1043533
Notes
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Reaction equation

HRID 1043533 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:24]=[CH:23][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][C:20](O)=[O:21])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.S(Cl)([Cl:29])=O>>[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:24]=[CH:23][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][C:20]([Cl:29])=[O:21])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 866859063-(2-(4-(4-(Trifluoromethoxy)phenoxy)piperidin-1-yl)ethoxy)propionic acid

Product 1

HCID 866859053-(2-(4-(4-(Trifluoromethoxy)phenoxy)piperidin-1-yl)ethoxy)propionyl chlorideYield 100%

Procedure

3-(2-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl)ethoxy)propionic acid (377 mg, 1.0 mmol) was dissolved in thionyl chloride, raised the temperature to reflux for 3 h, spun dry, residuals were washed by an appropriate amount of ethyl ether, generated 395 mg target product, yield was 100%, directly put to the next reaction step.

Workup

  1. temperatureraised the temperature
  2. temperature
to reflux for 3 h
  • customspun dry
  • washresiduals were washed by an appropriate amount of ethyl ether
  • customdirectly put to the next reaction step
  • Sources & evidence

    ORD record
    ord-c6e0f9cd328e4667b6ed65f429b98c2c
    Source dataset
    uspto-grants-2013_10
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08563547B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes