Dimethyl Sulfoxide → HCID 13035939, compound

HRID 1248235Notes

Reaction equation

HRID 1248235 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-448bae5dd47c4bc280ff28bdc03ebb29
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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