Triethylamine → HCID 21504633, Verbindung

HRID 1288225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1288225
Cl.[NH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([S:11]([NH2:14])(=[O:13])=[O:12])[CH2:7][CH2:6]1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29](Cl)=[O:30])[CH:24]=1>Cl.O1CCCC1>[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29]([NH:2][CH2:3][CH2:4][CH:5]2[CH2:10][CH2:9][N:8]([S:11]([NH2:14])(=[O:13])=[O:12])[CH2:7][CH2:6]2)=[O:30])[CH:24]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 110951464-chloropyridine-2-carbonyl ChlorideHCID 122820794-(2-Aminoethyl)piperidine-1-sulfonamide hydrochloride

Produkt 1

HCID 21504633HCID 21504633, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of 1.95 g. (0.008 mole) of 4-(2-aminoethyl)-1-piperidinesulfonamide hydrochloride and 2.22 ml. (0.016 mole) of triethylamine in 15 ml. of dry tetrahydrofuran, there were added 1.41 g. (0.008 mole) of 4-chloropicolinoyl chloride dissolved in 15 ml. of tetrahydrofuran. The initial addition step was slightly exothermic (~40° C.) and after completion of same, the resulting reaction mixture was stirred at ambient temperatures for a period of approximately 16 hours. At this point, the thoroughly stirred mixture was poured into 50 ml. of ice water and subsequently acidified with a few drops of 3N aqueous hydrochloric acid. The resulting crystalline precipitate was then recovered by means of suction filtration and thereafter recrystallized twice from acetonitrile to afford 0.997 g. of pure product. In this way, there was ultimately obtained a 36% of 4-[2-(4-chloropicolinamido)ethyl]-1-piperidinesulfonamide, m.p. 186°-187° C.

Aufarbeitung

  1. additionTo a mixture of 1.95 g
  2. additionThe initial addition step
  3. custom(~40° C.)
  4. customafter completion of same, the resulting reaction mixture
  5. additionAt this point, the thoroughly stirred mixture was poured into 50 ml
  6. filtrationThe resulting crystalline precipitate was then recovered by means of suction filtration
  7. customrecrystallized twice from acetonitrile
  8. customto afford 0.997 g

Quellen und Nachweise

ORD-Eintrag
ord-4627c0877bd944ceadec2e5e00886e46
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03987172

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