Thionyl Chloride → HCID 57966568, compound

HRID 420582Notes

Reaction equation

HRID 420582 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][C:12]([CH2:17][CH2:18]O)([CH2:15][CH3:16])[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.S(Cl)([Cl:24])=O>>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][C:12]([CH2:17][CH2:18][Cl:24])([CH2:15][CH3:16])[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 579667042-[1-(6-Chlorobenzothiazole-2-yl)-4-ethyl piperidine-4-yl]ethanol

Product 1

HCID 57966568HCID 57966568, compoundYield 92%

Conditions

Temperature
60 °C

Procedure

A mixture of 2-[1-(6-chlorobenzothiazole-2-yl)-4-ethyl piperidine-4-yl]ethanol (764 mg) and thionyl chloride (4 mL) were stirred at 60° C. for 1.5 hours. To the reaction solution was added ice and extracted with ethyl acetate. The organic layer was washed with sodium hydrogencarbonate and brine and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (739 mg). Yield: 92%.

Workup

  1. additionTo the reaction solution was added ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with sodium hydrogencarbonate and brine
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-3a597c77aaf34956b6c42a84b3d5e76d
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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