Dimethyl Sulfoxide → HCID 13035939, compound

HRID 1156349Notes

Reaction equation

HRID 1156349 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)C#N)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CS(C)=[O:26]>>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([C:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[O:26])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 202789461-(Phenylmethyl)-alpha-(2-thienyl)-4-piperidineacetonitrile

Product 1

HCID 13035939HCID 13035939, compoundYield 35%

Procedure

To a stirred mixture of 29.6 parts of 1-(phenylmethyl)-α-(2-thienyl)-4-piperidineacetonitrile in 100 parts of dimethyl sulfoxide are added portionwise 4 parts of sodium hydride dispersion 60%. Upon completion, stirring is continued overnight. The reaction mixture is poured onto water. The precipitated product is sucked off and extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane, yielding 10 parts (35%) of [1-(phenylmethyl)-4-piperidinyl] (2-thienyl) methanone; mp. 100.5° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionextracted with trichloromethane
  3. customThe extract is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-1932858c4dfd4bc9b77d6f2e57bfb508
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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