p-Toluenesulfonic acid → HCID 14770819, compound

HRID 1651599Notes

Reaction equation

HRID 1651599 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2(O)[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[C:4]([F:21])[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH:10]=2)=[C:4]([F:21])[CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14770818HCID 14770818, compound

Product 1

HCID 14770819HCID 14770819, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.12 g (30.5 mmol) 4-(4-bromo-2,5-difluorophenyl)-1-ethoxycarbonyl-4-piperidinol and 0.70 g of p-toluenesulfonic acid in 200 ml toluene was refluxed with a Dean-Stark trap for 16 hours. The mixture was cooled, extracted with sodium bicarbonate solution, dried (MgSO4), evaporated and the residue flash chromatographed on a column of silica gel to afford a syrup which crystallized on standing, mp 40°-44° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customthe residue flash chromatographed on a column of silica gel
  6. customto afford a syrup which
  7. customcrystallized on standing, mp 40°-44° C.

Sources & evidence

ORD record
ord-5f3fa3953bc74ab392a3a232a39f03b9
Source dataset
uspto-grants-1990_05
Patent number
US04929613

Reaction notes

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