HCID 178456134, compound → HCID 178472364, compound

HRID 1979964Notes

Reaction equation

HRID 1979964 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1)#[N:2].[C:12]([C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH:23](Cl)[CH3:24])=[O:21])[CH2:16][CH2:15]1)#[N:13]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[C:1]([C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH:23]([O:22][C:20]([C@H:17]2[CH2:18][CH2:19][C@H:14]([C:12]#[N:13])[CH2:15][CH2:16]2)=[O:21])[CH3:24])=[O:10])[CH2:7][CH2:8]1)#[N:2]

Participants

5

Reactant 2

HCID 178456134HCID 178456134, compoundHCID 178511260HCID 178511260, compound

Product 1

HCID 178472364HCID 178472364, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 14798Sodium HydroxideSolvent

Procedure

Trans-4-cyanocyclohexanecarboxylic acid (11.5 g; 0.075 mol) and tetrabutylammonium hydrogen sulfate (25.5 g; 0.075 mol) was dissolved in 2M sodium hydroxide and extracted with ethanolfree chloroform. The chloroform solution was dried and the solvent evaporated. The residue was dissolved in trichloroethylene (600 ml) and 1-(trans-4-cyanocyclohexanoyloxy)ethyl chloride (10.8 g; 0.05 mol) was added. The solution was refluxed for 8 h. It was then washed, dried and evaporated. Yield 17.1 g, m.p. 75°-76° C.

Workup

  1. extractionextracted with ethanolfree chloroform
  2. dry with materialThe chloroform solution was dried
  3. customthe solvent evaporated
  4. dissolutionThe residue was dissolved in trichloroethylene (600 ml)
  5. temperatureThe solution was refluxed for 8 h
  6. washIt was then washed
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-7b9ab7eceda545948a39341a970df9aa
Source dataset
uspto-grants-1984_11
Patent number
US04483867

Reaction notes

Loading…