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

HRID 1043533Notes

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

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. temperatureto reflux for 3 h
  3. customspun dry
  4. washresiduals were washed by an appropriate amount of ethyl ether
  5. customdirectly put to the next reaction step

Sources & evidence

ORD record
ord-c6e0f9cd328e4667b6ed65f429b98c2c
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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