Potassium Iodide → 4-(2,3,4-Trimethoxybenzylthio)-1-cinnamylpiperidine fumarate

HRID 893828Notes

Reaction equation

HRID 893828 reaction equation
[CH3:1][O:2][C:3]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:4]=1[CH2:5][S:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH2:21](Br)[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:39]([O-:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([O-:44])=[O:43]>CC#N.C(O)C>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43].[CH3:1][O:2][C:3]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:4]=1[CH2:5][S:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:21][CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:9][CH2:8]1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 98116BromomethylstyreneHCID 5460307FumarateHCID 198909314-(2,3,4-Trimethoxybenzylthio)piperidine

Product 1

HCID 678945404-(2,3,4-Trimethoxybenzylthio)-1-cinnamylpiperidine fumarate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 10 g of 4-(2,3,4-trimethoxybenzylthio)piperidine and 6.62 g of cinnamyl bromide in 300 ml of CH3CN is heated under reflux for 15 hours in the presence of 4.64 g of potassium carbonate and 0.5 g of potassium iodide. The salt is then filtered off and the filtrate is evaporated under reduced pressure. The residue is taken up in CH2Cl2 --H2O and, after decantation, the ichloromethane phase is dried over Na2SO4 and evaporated under reduced pressure. The resulting residue (15 g) is purified by chromatography on 600 g of silica with a toluene-methanol (95-5) system, yielding 10 g of crude base, which is converted into the fumarate in an ethanol medium. 7 g of 4-(2,3,4-trimethoxybenzylthio)-1-cinnamylpiperidine fumarate are obtained in the form of white crystals which melt at 129° C.

Workup

  1. temperatureis heated
  2. filtrationThe salt is then filtered off
  3. customthe filtrate is evaporated under reduced pressure
  4. dry with materialH2O and, after decantation, the ichloromethane phase is dried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe resulting residue (15 g) is purified by chromatography on 600 g of silica with a toluene-methanol (95-5) system
  7. customyielding 10 g of crude base, which

Sources & evidence

ORD record
ord-df71243b8a3b4386b631c3d083f197e6
Source dataset
uspto-grants-1992_06
Patent number
US05126356

Reaction notes

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