3,5-Diamino-1,2,4-triazole → HCID 178509286, Verbindung

HRID 2058737

Reaktionsgleichung

Reaktionsgleichung von HRID 2058737
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][CH2:13][CH2:14][CH:15]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:20][C:21]1[N:25]=[C:24]([NH2:26])[NH:23][N:22]=1.[BH4-].[Na+]>C(O)C>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:26][C:24]2[NH:23][N:22]=[C:21]([NH2:20])[N:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 150783,5-Diamino-1,2,4-triazoleHCID 4311764Sodium borohydrideHCID 212975474-[3-(1-Piperidinylmethyl)phenoxy]butanal

Produkt 1

HCID 178509286HCID 178509286, VerbindungAusbeute 36,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 4-[3-(1-piperidinylmethyl)phenoxy]butanal (522 mg) and 3,5-diamino-1,2,4-triazole (200 mg) in absolute ethanol (20 ml) was heated under reflux for 2 h. The cooled solution was treated with sodium borohydride (200 mg) and stirred at room temperature for 18 hr. The mixture was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The combined organic extracts were evaporated in vacuo and the residue was chromatographed on silica with methanol as eluant to give the title compound as an oil (250 mg), TLC silica (ethyl acetate:isopropanol:water:ammonia 25:15:8:2) 0.4, NMR (CDCl3) 2.8 t (1H); 3.0-3.3 m (3H); 5.3 m (2H); 6.2 m (2H); 6.6-6.8 m (4H); 7.7 m (4H); 8.0-8.8 m (10H).

Aufarbeitung

  1. temperatureunder reflux for 2 h
  2. customThe mixture was evaporated in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe combined organic extracts were evaporated in vacuo
  5. customthe residue was chromatographed on silica with methanol as eluant

Quellen und Nachweise

ORD-Eintrag
ord-c1ab0e48a8f741f493bda1ccc1800c3c
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04318913

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