Triethylamine → HCID 39240504, compound

HRID 551158Notes

Reaction equation

HRID 551158 reaction equation
[Cl-].[C:2]([CH:4]1[CH2:9][CH2:8][NH2+:7][CH2:6][CH2:5]1)#[N:3].C(N(CC)CC)C.[CH2:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18]>ClCCl>[CH2:17]([S:19]([N:7]1[CH2:8][CH2:9][CH:4]([C:2]#[N:3])[CH2:5][CH2:6]1)(=[O:21])=[O:20])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 178510228HCID 178510228, compound

Product 1

HCID 39240504HCID 39240504, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dry round bottom flask was placed 4-cyanopiperidinium chloride (13, 5 g, 45.4 mmol) dichloromethane (150 ml) and triethylamine (18.98 ml, 136 mmol). To the reaction was added dropwise ethanesulfonyl chloride (4.56 ml, 45.4 mmol) and the solution stirred 1 hour and quenched with water (100 ml). The mixture was extracted with dichloromethane (3×50 ml) and the combined organic fractions dried (MgSO4), filtered, and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with EtOAc/Hexanes to give 1-(ethylsulfonyl)piperidine-4-carbonitrile (14) as a white solid. MS 203 (M+1)

Workup

  1. customIn a dry round bottom flask was placed
  2. customquenched with water (100 ml)
  3. extractionThe mixture was extracted with dichloromethane (3×50 ml)
  4. dry with materialthe combined organic fractions dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with EtOAc/Hexanes

Sources & evidence

ORD record
ord-be6d3dbf4ae249acba17d0efe653ddbe
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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