Hydrochloric Acid → HCID 11715586, compound

HRID 1437742Notes

Reaction equation

HRID 1437742 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[C:12](Cl)[CH:11]=[C:10]([Cl:15])[N:9]=1.Cl>C1COCC1.[OH-].[Na+]>[Cl:7][C:8]1[CH:13]=[C:12]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:11]=[C:10]([Cl:15])[N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 27665Pyridine, 2,4,6-trichloro-

Product 1

HCID 11715586HCID 11715586, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of piperidine (0.910 g, 10.7 mmol) in 25 mL of THF and 5 mL of 1N NaOH was stirred for 30 minutes at 0° C., after which time 2,4,6-trichloropyridine (1.63 g, 8.86 mmol) was added. The reaction mixture was then stirred at 30-40° C. for 12-18 hours, after which the reaction mixture was cooled and neutralized with 5% HCl (aq). This product was extracted with ethyl acetate, and the organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography over 100-200 mesh silica gel by elution with 10:90 ethyl acetate: hexanes to afford the product as a pure colorless solid (yield 32%).

Workup

  1. stirringThe reaction mixture was then stirred at 30-40° C. for 12-18 hours
  2. temperatureafter which the reaction mixture was cooled
  3. extractionThis product was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over 100-200 mesh silica gel by elution with 10:90 ethyl acetate

Sources & evidence

ORD record
ord-c69ad118b43a49fabadaf102f8ee7ed0
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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