Hydrochloric Acid → HCID 70394800, compound

HRID 1721893Notes

Reaction equation

HRID 1721893 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]([C:8]1[CH:9]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:10]([C:16]([O:18][CH3:19])=[O:17])=[C:11]([CH3:15])[NH:12][C:13]=1[CH3:14])=[O:7].[F:29][C:30]1[CH:43]=[CH:42][C:33]([C:34]([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[O:35])=[CH:32][CH:31]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C(OCC)(=O)C>[F:29][C:30]1[CH:31]=[CH:32][C:33]([C:34]([CH:36]2[CH2:41][CH2:40][N:39]([CH2:2][CH2:3][CH2:4][O:5][C:6]([C:8]3[CH:9]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=4)[C:10]([C:16]([O:18][CH3:19])=[O:17])=[C:11]([CH3:15])[NH:12][C:13]=3[CH3:14])=[O:7])[CH2:38][CH2:37]2)=[O:35])=[CH:42][CH:43]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 10740240HCID 10740240, compound

Product 1

HCID 70394800HCID 70394800, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 16.4 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 3-chloropropyl ester and 16.6 g of 4-(p-fluorobenzoyl)-piperidine is kept for 1 hour under argon in a bath heated to 145°. After cooling, 100 ml of ethyl acetate and 50 ml of 2N hydrochloric acid are added and the mixture is stirred until the reaction mass has completely dissolved. The partly oily aqueous-acidic phase is adjusted to pH 10 with 50% potassium carbonate solution; methylene chloride is added and the whole is filtered with suction. The methylene chloride phase of the filtrate is separated off and concentrated by evaporation and the residue is dissolved in ethyl acetate; the solution is dried over sodium sulphate and filtered. Filtration is then carried out over 1 kg of silica gel Merck 9385 using a hexane/ethyl acetate/methanol mixture (4:2:0.5) as eluant. The 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 3-[4-(p-fluorobenzoyl)-piperidino]-propyl ester obtained after working up is converted by means of ethereal hydrogen chloride solution into the hydrochloride which, after recrystallisation from isopropanol, melts at 198°-205° with the evolution of gas.

Workup

  1. temperatureheated to 145°
  2. temperatureAfter cooling
  3. dissolutionhas completely dissolved
  4. filtrationthe whole is filtered with suction
  5. customThe methylene chloride phase of the filtrate is separated off
  6. concentrationconcentrated by evaporation
  7. dissolutionthe residue is dissolved in ethyl acetate
  8. dry with materialthe solution is dried over sodium sulphate
  9. filtrationfiltered
  10. filtrationFiltration

Sources & evidence

ORD record
ord-8c6c6d28caf548e28f2807a1b13ac1ff
Source dataset
uspto-grants-1989_08
Patent number
US04853393

Reaction notes

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