Ammonium Chloride → HCID 68551762, compound

HRID 1868050Notes

Reaction equation

HRID 1868050 reaction equation
[C:1]1([S:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:17]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=1.C(N(C(C)C)CC)(C)C.[NH4+].[Cl-]>O1CCOCC1>[C:1]1([S:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:17]3[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:14][CH2:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 5190868HCID 5190868, compound

Product 1

HCID 68551762HCID 68551762, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a microwave vial were charged 4-(phenylsulfonyl)piperidine (300 mg, 1.33 mmol), 2-chloro-3-(trifluoromethyl)pyridine, (484 mg, 2.66 mmol), diisopropylethylamine (0.695 mL, 3.99 mmol) and 1,4-Dioxane (0.2 mL). The reaction mixture thus prepared was irradiated at 200° C. for 1 hour. The reaction was complete as determined by TLC. The residue was added with saturated NH4Cl (aq.) and extracted with ethylacetate, washed with 10% HCl (aq.), water then brine. Organic layer was dried over MgSO4. Solvent evaporation afforded 2-[4-(phenylsulfonyl)piperidin-1-yl]-3-(trifluoromethyl)pyridine in 55% yield (270 mg) as white solid.

Workup

  1. customThe reaction mixture thus prepared
  2. customwas irradiated at 200° C. for 1 hour
  3. extractionextracted with ethylacetate
  4. washwashed with 10% HCl (aq.), water
  5. dry with materialOrganic layer was dried over MgSO4
  6. customSolvent evaporation

Sources & evidence

ORD record
ord-570587f1a97d462da435cce6022d79cd
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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