Hydrogen Bromide → HCID 20511831, compound

HRID 1164361Notes

Reaction equation

HRID 1164361 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]2([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:13][CH2:12][N:11](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:10][CH2:9]2)[CH:7]=1.C1(O)C=CC=CC=1.Br>C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]2([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 20511808HCID 20511808, compound

Product 1

HCID 20511831HCID 20511831, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 17 parts of ethyl 4-(5-chloro-2-methoxyphenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarboxylate, 7.5 parts of phenol and 135 parts of a hydrobromic acid solution in acetic acid is stirred overnight at room temperature. The reaction mixture is poured onto water and the whole is washed with 2,2'-oxybispropane. The aqueous phase is alkalized with sodium hydroxide while cooling. The product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanol and 2,2'-oxybispropane, yielding 7 parts (55%) of ethyl 4-(5-chloro-2-methoxyphenyl)-4-piperidinecarboxylate hydrochloride.

Workup

  1. additionThe reaction mixture is poured onto water
  2. washthe whole is washed with 2,2'-oxybispropane
  3. temperaturewhile cooling
  4. extractionThe product is extracted with trichloromethane
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a60957fdeb9b40a5aacf6418592ea519
Source dataset
uspto-grants-1983_01
Patent number
US04369184

Reaction notes

Loading…