Toluene → HCID 20388043, compound

HRID 1390318Notes

Reaction equation

HRID 1390318 reaction equation
S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-])(=O)=O.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CCOCC.[C:23]1(C)[CH:28]=CC=[CH:25][CH:24]=1>>[CH2:9]1[C:8]2[C:7](=[CH:6][CH:5]=[CH:11][CH:10]=2)[C:23]([CH2:24][CH2:25][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:28]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 8082PiperidineHCID 85570p-Toluenesulfonate

Product 1

HCID 20388043HCID 20388043, compoundYield 99%

Procedure

The crude tosylate prepared as described in part B above (41.5 g, 0.13 M) and piperidine (28 g, 0.33 M) in 200 ml toluene are heated under reflux overnight. Ether is added to the warm reaction mixture until crystals begin forming. After cooling, the solid is removed by filtration and washed several times with ether. The filtrate and washes are combined and the solvents removed in vacuo. The oily residue is dissolved in ether, a small amount of insoluble material is removed by filtration, and the ether is removed from the filtrate leaving 29.7 g (99%) of brown oil. The sample is purified by distillation at reduced pressure recovering 86% as a yellow oil boiling in 115°/0.05 mm. to 130°/0.1 mm.

Workup

  1. temperatureare heated
  2. temperatureunder reflux overnight
  3. custombegin forming
  4. temperatureAfter cooling
  5. customthe solid is removed by filtration
  6. washwashed several times with ether
  7. customthe solvents removed in vacuo
  8. dissolutionThe oily residue is dissolved in ether
  9. customa small amount of insoluble material is removed by filtration
  10. customthe ether is removed from the filtrate

Sources & evidence

ORD record
ord-2f4daa327a0144b88868131f7f623a51
Source dataset
uspto-grants-1979_02
Patent number
US04138497

Reaction notes

Loading…