Potassium Iodide → HCID 57115188, compound

HRID 648635Notes

Reaction equation

HRID 648635 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]([CH:15]([C:24]([NH2:26])=[O:25])[C:16]2[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=2)[CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[CH2:31]([O:33][C:34](=[O:41])[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:32].[Na].[Na].C(OC(=O)CC(OCC)=O)C.[I-].[K+]>C(Cl)(Cl)Cl.C(O)C>[CH2:31]([O:33][C:34](=[O:41])[CH:35]([CH2:20][C:19]1[CH:22]=[CH:23][C:16]([CH:15]([CH:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH3:14])[C:24]([NH2:26])=[O:25])=[CH:17][CH:18]=1)[C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:32]

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 7761Diethyl MalonateHCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 20145263HCID 20145263, compoundHCID 86602522HCID 86602522, compound

Product 1

HCID 57115188HCID 57115188, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 3.7 gm (10 m mol) of 4-[(1-(2-piperidinophenyl)-ethyl)-aminocarbonylmethyl]-benzyl chloride [m.p.: 123°-125° C.; prepared from the alcohol described in Example 25 by means of thionyl chloride in chloroform] in 35 ml of absolute ethanol was added dropwise to a solution of sodium malonic acid diethyl ester [prepared from 0.7 gm (30 m mol) of sodium in 25 ml of absolute ethanol and 4.8 gm (30 m mol) of malonic acid diethyl ester]. A catalytic amount of potassium iodide was added, and the mixture was refluxed for 16 hours. After evaporation in vacuo, the evaporation residue was adjusted neutral by means of hydrochloric acid and extracted with methylene chloride. The organic extract was dried over sodium sulfate, filtered, and evaporated in vacuo. The evaporation residue was purified by column chromatography on silica gel (toluene/acetone=6:1).

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. customAfter evaporation in vacuo
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe evaporation residue was purified by column chromatography on silica gel (toluene/acetone=6:1)

Sources & evidence

ORD record
ord-7626ae9b2c334a888574a9918efee351
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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