Dimethyl Sulfoxide → 1-Boc-4-cyano-4-(4-pyridinyl)-piperidine

HRID 1800826Notes

Reaction equation

HRID 1800826 reaction equation
Cl.[C:2]([CH2:4][C:5]1[CH:10]=[CH:9][NH+:8]=[CH:7][CH:6]=1)#[N:3].Cl[CH2:12][CH2:13][N:14]([CH2:22][CH2:23]Cl)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>C(OCC)(=O)C>[C:2]([C:4]1([C:5]2[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=2)[CH2:23][CH2:22][N:14]([C:15]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:21])[CH2:13][CH2:12]1)#[N:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amineHCID 86641590HCID 86641590, compound

Product 1

HCID 539443251-Boc-4-cyano-4-(4-pyridinyl)-piperidineYield 41.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Cyanomethylpyridinium hydrochloride (1.0 g, 6.5 mmol), 2.0 g tert-butyl bis(2-chloroethyl)carbamate (J. Med. Chem. 1992, 35, 11, 2033-2039) (8.1 mmol), 9.1 g caesium carbonate (28 mmol) and 20 ml DMSO were combined in a round bottom flask and stirred at room temperature for 20 hours. The reaction mixture was diluted with ethyl acetate and the organic layer washed with water, then brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The product was purified by column chromatography on silica, using a gradient from 10% to 100% ethyl acetate in hexanes as eluent. 778 mg of the title compound were isolated as an oil (42% yield)

Workup

  1. washthe organic layer washed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-4e1a44ff0ee141ca882fdde2510a3006
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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