Potassium Carbonate → HCID 20232620, compound

HRID 2290467Notes

Reaction equation

HRID 2290467 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[CH2:8][CH2:9]OS(C1C=CC(C)=CC=1)(=O)=O)([CH3:4])([CH3:3])[CH3:2].[N:29]1([CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:39][CH:38]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:25]([C:22]1[CH:21]=[C:7]([CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:23]=1[OH:24])[CH2:8][CH2:9][N:32]1[CH2:33][CH2:34][N:29]([CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:39][CH:38]=2)[CH2:30][CH2:31]1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 616056HCID 616056, compoundHCID 20232558HCID 20232558, compound

Product 1

HCID 20232620HCID 20232620, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 13.9 g. (50.2 mmole) p-toluenesulphonic acid (3,5-di-tert.-butyl-4-hydroxyphenethyl)ester, 18.4 g. (45.6 mmole) ethyl 4-[2-(piperazin-1-yl)-ethyl]-phenylacetate, 6.3 g. potassium carbonate and 300 ml. butan-2-one is heated for 8 hours while stirring at reflux temperature. For protection against oxidation, the reaction is carried out under an atmosphere of nitrogen. After cooling, the inorganic precipitate is filtered off with suction, the filtrate is evaporated and the evaporation residue is taken up in diethyl ether. From the ether solution, the hydrochloride is precipitated with hydrogen chloride-containing diethyl ether. After recrystallisation from ethanol, there are obtained 16.4 g. (62% of theory) of the desired compound as hydrochloride; m.p. 247°-250° C.

Workup

  1. additionA mixture of 13.9 g
  2. temperatureat reflux temperature
  3. temperatureAfter cooling
  4. filtrationthe inorganic precipitate is filtered off with suction
  5. customthe filtrate is evaporated
  6. customFrom the ether solution, the hydrochloride is precipitated with hydrogen chloride-
  7. additioncontaining diethyl ether
  8. customAfter recrystallisation from ethanol, there
  9. customare obtained 16.4 g

Sources & evidence

ORD record
ord-1846c29fc1f34e7b9ed9d84f5ff3eb31
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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