Pyridine → HCID 56617074, compound

HRID 2290460Notes

Reaction equation

HRID 2290460 reaction equation
Cl.Cl.[N:3]1([CH2:9][CH2:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.N1C=CC=CC=1.[C:28]([C:32]1[CH:33]=[C:34]([CH:40]=[C:41]([C:44]([CH3:47])([CH3:46])[CH3:45])[C:42]=1[OH:43])[CH:35]=[CH:36][C:37](Cl)=[O:38])([CH3:31])([CH3:30])[CH3:29]>C1C=CC=CC=1>[C:44]([C:41]1[CH:40]=[C:34]([CH:33]=[C:32]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:42]=1[OH:43])[CH:35]=[CH:36][C:37]([N:6]1[CH2:7][CH2:8][N:3]([CH2:9][CH2:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH2:4][CH2:5]1)=[O:38])([CH3:46])([CH3:47])[CH3:45]

Participants

5

Reactant 3

HCID 1049PyridineHCID 20232631HCID 20232631, compoundHCID 54252998HCID 54252998, compound

Product 1

HCID 56617074HCID 56617074, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of 16.8 g. (50 mmole) ethyl 4-[2-(piperazin-1-yl)-ethyl]-benzoate dihydrochloride and 200 ml. anhydrous pyridine is added dropwise at 5°-10° C., in the course of 40 minutes, a solution of 14.8 g. 3,5-di-tert.-butyl-4-hydroxycinnamoyl chloride and 50 ml. anhydrous benzene. The reaction mixture is stirred for 4 hours at 20° C., the benzene and pyridine are substantially distilled off in a vacuum and the residue is stirred into about 1 liter ice water. The separated, greasy precipitate is taken up in methylene chloride and the methylene chloride phase is washed with aqueous sodium carbonate solution, dried with anhydrous sodium sulphate and evaporated to dryness in a vacuum. The crude base is dissolved in ethanol, gassed with hydrogen chloride and finally precipitated as the hydrochloride by the addition of diethyl ether. The yield is 17.3 g. (62% of theory) of the desired product which, after stirring up with diethyl ether, melts at 193°-195° C. (decomp.).

Workup

  1. additionTo a mixture of 16.8 g
  2. distillationthe benzene and pyridine are substantially distilled off in a vacuum
  3. stirringthe residue is stirred into about 1 liter ice water
  4. washthe methylene chloride phase is washed with aqueous sodium carbonate solution
  5. dry with materialdried with anhydrous sodium sulphate
  6. customevaporated to dryness in a vacuum
  7. dissolutionThe crude base is dissolved in ethanol
  8. customfinally precipitated as the hydrochloride by the addition of diethyl ether
  9. stirring(62% of theory) of the desired product which, after stirring up with diethyl ether, melts at 193°-195° C. (decomp.)

Sources & evidence

ORD record
ord-dd767497371f46b8ab038154220ed964
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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