Potassium Carbonate → HCID 20232465, compound

HRID 2290464Notes

Reaction equation

HRID 2290464 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[C:12]([C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]=1[OH:25])[CH2:19][CH2:20]O)([CH3:15])([CH3:14])[CH3:13].[N:30]1([C:36]2[CH:41]=[CH:40][C:39]([CH2:42][C:43]([O:45][CH2:46][CH2:47][CH2:48][CH3:49])=[O:44])=[CH:38][CH:37]=2)[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:26]([C:23]1[CH:22]=[C:18]([CH:17]=[C:16]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:24]=1[OH:25])[CH2:19][CH2:20][N:33]1[CH2:32][CH2:31][N:30]([C:36]2[CH:37]=[CH:38][C:39]([CH2:42][C:43]([O:45][CH2:46][CH2:47][CH2:48][CH3:49])=[O:44])=[CH:40][CH:41]=2)[CH2:35][CH2:34]1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 85570p-ToluenesulfonateHCID 794359HCID 794359, compoundHCID 20232546HCID 20232546, compound

Product 1

HCID 20232465HCID 20232465, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 20.2 g. (50 mmole) of the tosylate of 3,5-di-tert.-butyl-4-hydroxyphenethyl alcohol, 13.8 g. (50 mmole) n-butyl 4-(piperazin-1-yl)-phenylacetate, 6.9 g. (50 mmole) powdered anhydrous potassium carbonate and 200 ml. butan-2-one is maintained at reflux temperature for 24 hours, then suction filtered hot and the filtrate evaporated in a vacuum. The residue is taken up in diethyl ether, the ether phase is extracted twice with water, then dried with anhydrous sodium sulphate and evaporated. By means of ligroin, the product is brought to crystallisation and recrystallised from n-butanol. Yield 14.3 g. (59% of theory); m.p. 103°-105° C.

Workup

  1. additionA mixture of 20.2 g
  2. temperatureat reflux temperature for 24 hours
  3. filtrationsuction filtered hot
  4. customthe filtrate evaporated in a vacuum
  5. extractionthe ether phase is extracted twice with water
  6. dry with materialdried with anhydrous sodium sulphate
  7. customevaporated
  8. customBy means of ligroin, the product is brought to crystallisation
  9. customrecrystallised from n-butanol

Sources & evidence

ORD record
ord-5b2eea36891949e6bec4106e3ceaa218
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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