Triethylamine → Ethyl 1-benzyl-4-(1,2,4-triazol-1-yl)-piperidin-4-yl carboxylate

HRID 1602327Notes

Reaction equation

HRID 1602327 reaction equation
Cl.Cl.[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([NH:16][NH2:17])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23][N:24](C=NC=[N+](C)C)[CH3:25].[Cl-].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH2:3]([N:10]1[CH2:11][CH2:12][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([N:16]2[CH:25]=[N:24][CH:23]=[N:17]2)[CH2:14][CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 11008255Gold's ReagentHCID 19610927HCID 19610927, compound

Product 1

HCID 15663646Ethyl 1-benzyl-4-(1,2,4-triazol-1-yl)-piperidin-4-yl carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred suspension of ethyl 1-benzyl-4-hydrazinopiperdin-4-ylcarboxylate dihydrochloride salt (D27, 2.0 g, 0.0057 mol) in absolute chloroform (200 ml) was treated with Gold's reagent ([3-(dimethylamino)-2-azaprop-2-en-1-ylidene]-dimethylammonium chloride) (930 mg, 0.0057 mol) and triethylamine (1.6 ml, 0.0114 mol) and the mixture heated at reflux under nitrogen for 2.5 h. The solution was allowed to cool, treated with concentrated potassium carbonate solution and the organic layer separated, dried (Na2SO4) and concentrated in vacuo to leave an orange oil. This was chromatographed on silica gel eluting first with ethyl acetate to obtain the title compound (D28), then with methanol to obtain a high polar intermediate, which on heating under reflux in toluene for 20 minutes gave a further batch of the triazole product. These two batches were combined to give the title compound (D28) (770 mg, 43%) as an orange oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux under nitrogen for 2.5 h
  3. temperatureto cool
  4. customthe organic layer separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto leave an orange oil
  8. customThis was chromatographed on silica gel eluting first with ethyl acetate

Sources & evidence

ORD record
ord-6a8f5cfbc83b466fbcbfb1a1ac5c8ec4
Source dataset
uspto-grants-1999_11
Patent number
US05981545

Reaction notes

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