Tosylmethyl isocyanide → HCID 66798807, compound

HRID 1193327Notes

Reaction equation

HRID 1193327 reaction equation
C(O[K])(C)(C)C.[N:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.CC1C=CC(S([CH2:30][N+:31]#[C-])(=O)=O)=CC=1>COCCOC.CCO>[N:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:30]#[N:31])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 113327931-(Pyridin-4-yl)piperidin-4-oneHCID 178418922HCID 178418922, compound

Product 1

HCID 66798807HCID 66798807, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

tBuOK (2.29 g, 20.45 mmol, 2.5 eq) was added in portions at −5° C. to a solution of 1-(pyridin-4-yl)piperidin-4-one (1.44 g, 8.18 mmol, 1 eq) and TOSMIC (1.91 g, 9.81 mmol, 1.2 eq) in DME (20 ml) and EtOH (0.5 ml), and then stirring was carried out for 2 h at RT. The reaction mixture was hydrolyzed with ice-water (50 ml), extracted with dichloromethane (2×100 ml). The combined organic phases were washed with water and sat. NaCl solution (in each case 100 ml), dried over sodium sulfate and concentrated under reduced pressure. After purification by column chromatography (silica gel, 4% MeOH in dichloromethane), the desired product was obtained in the form of a brown solid. Yield: 34% (530 mg, 2.83 mmol).

Workup

  1. extractionextracted with dichloromethane (2×100 ml)
  2. washThe combined organic phases were washed with water and sat. NaCl solution (in each case 100 ml),
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customAfter purification by column chromatography (silica gel, 4% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-5b31e07a762e49a8bf6ec614180e396a
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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