Triethylamine → HCID 57931193, compound

HRID 551150Notes

Reaction equation

HRID 551150 reaction equation
[Cl-].[C:2]([C:4]1([CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:9][CH2:8][NH2+:7][CH2:6][CH2:5]1)#[N:3].C(N(CC)CC)C.[CH2:21]([S:23](Cl)(=[O:25])=[O:24])[CH3:22]>ClCCl>[CH2:21]([S:23]([N:7]1[CH2:8][CH2:9][C:4]([CH2:10][CH:11]([CH3:13])[CH3:12])([C:2]#[N:3])[CH2:5][CH2:6]1)(=[O:25])=[O:24])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 67173209HCID 67173209, compound

Product 1

HCID 57931193HCID 57931193, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dry round bottom flask was placed 4-cyano-4-isobutylpiperidinium chloride (3, 4.49 g, 44.4 mmol) dichloromethane (150 ml) and triethylamine (6.1 ml, 44.4 mmol). To this was added dropwise ethanesulfonyl chloride (2.1 ml, 22.2 mmol). This was 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 evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with EtOAc/Hexanes to give 1-(ethylsulfonyl)-4-isobutylpiperidine-4-carbonitrile (4) as a white solid. MS 259 (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. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with EtOAc/Hexanes

Sources & evidence

ORD record
ord-807653328de04a098a2f4fd253da4b28
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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