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

HRID 35069

Reaction equation

HRID 35069 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 178509286HCID 178509286, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ac2250f3300540b5b2478b32d0a569ab
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Linked notes

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