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1,1'-Carbonyldiimidazole → 3-[(4-Chlorophenyl)thio]-N-[2-(dimethylamino)ethyl]-1-piperidinecarboxamide Monohydrochloride

HRID 1981810
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1981810
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].[CH3:13]NN(CC)NC.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27][CH:28]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]2)=[CH:23][CH:22]=1>O1CCCC1>[ClH:20].[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([S:27][CH:28]2[CH2:33][CH2:32][CH2:31][N:30]([C:1]([NH:8][CH2:12][CH2:11][N:10]([CH3:9])[CH3:13])=[O:2])[CH2:29]2)=[CH:25][CH:26]=1
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Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 136079813-[(4-Chlorophenyl)thio]piperidineHCID 57041336N,N-Dimethylaminoethylamine

Produkt 1

HCID 202177703-[(4-Chlorophenyl)thio]-N-[2-(dimethylamino)ethyl]-1-piperidinecarboxamide Monohydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 5.70 g (0.0352 mole) of 1,1'-carbonyldiimidazole and 2.91 g (0.033 mole) of N,N-dimethylaminoethylamine in 200 ml of tetrahydrofuran was stirred at room temperature for 1.5 hr. A solution of 7.02 g (0.031 mole) of 3-[(4-chlorophenyl)thio]piperidine in 50 ml of tetrahydrofuran was added and the solution was refluxed for 10 hr. The volume of the reaction solution was reduced to about 50 ml in vacuo. The solution was quenched in water and the aqueous mixture was extracted with methylene chloride. The methylene chloride phase was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil, the free base of the title compound. The free base was converted to the hydrochloride salt and recrystallized as in Example 14 to give 8.48 g (72.3%) of white crystals, m.p. 175°-176.5° C.

Aufarbeitung

  1. temperaturethe solution was refluxed for 10 hr
  2. customThe solution was quenched in water
  3. extractionthe aqueous mixture was extracted with methylene chloride
  4. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-173a8edc6d5a4a1aa80ea8feaacf4c9f
Quelldatensatz
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04593102

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