Triethylamine → HCID 67174054, compound

HRID 551154Notes

Reaction equation

HRID 551154 reaction equation
[Cl-].[C:2]([C:4]1([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH2:9][CH2:8][NH2+:7][CH2:6][CH2:5]1)#[N:3].C(N(CC)CC)C.[CH2:24]([S:26](Cl)(=[O:28])=[O:27])[CH3:25]>ClCCl>[CH2:24]([S:26]([N:7]1[CH2:8][CH2:9][C:4]([CH2:10][CH:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)([C:2]#[N:3])[CH2:5][CH2:6]1)(=[O:28])=[O:27])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 67173445HCID 67173445, compound

Product 1

HCID 67174054HCID 67174054, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dry round bottom flask was placed 4-cyano-4-(tetrahydro-2H-pyran-4-ylmethyl)piperidinium chloride (9, 1 g, 3.1 mmol), dichloromethane (50 ml) and triethylamine (2.162 ml, 15.51 mmol). To this was added dropwise ethanesulfonyl chloride (0.317 ml, 3.1 mmol). The reaction was stirred 1 hour and quenched with water (100 ml). The mixture was extracted with dichloromethane (3×50 ml) and the combined organic fractions were 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)-4-(tetrahydro-2H-pyran-4-ylmethyl)piperidine-4-carbonitrile (10) as a white solid. MS 301 (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 were 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-b6595981b4d74f23b8c6ddda6380f886
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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