Ethyl 4-amino-1-piperidinecarboxylate → HCID 69055408, compound

HRID 1725762Notes

Reaction equation

HRID 1725762 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CN(C)/[CH:15]=[N:16]/[N:17]=[CH:18]/N(C)C>C1(C)C=CC=CC=1>[N:16]1[N:17]=[CH:18][N:12]([CH:9]2[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]2)[CH:15]=1

Participants

4

Reactant 2

HCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 9613942N'-((Dimethylamino)methylene)-N,N-dimethylformohydrazonamide

Product 1

HCID 69055408HCID 69055408, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of ethyl-4-amino-piperidine carboxylate (5 g, 29 mmol) in toluene (100 mL) was added N,N-dimethylformamide azine (8.2 g) and catalytic amount of p-tolunesulfonic acid (0.3 g) and the resulting mixture was refluxed overnight. The mixture was cooled and washed with water, and the aqueous layer was evaporated and the residue was treated with dichloromethane (100 mL). The organic layer was dried over MgSO4, filtered and evaporated. The residue was purified on silica flash column eluting with 4% MeOH, 0.5% NH4OH in dichloromethane to give the desired ethyl 4-(4H-1,2,4-triazol-4-yl)piperidine-1-carboxylate (4.9 g).

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. temperatureThe mixture was cooled
  3. washwashed with water
  4. customthe aqueous layer was evaporated
  5. additionthe residue was treated with dichloromethane (100 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on silica flash column
  10. washeluting with 4% MeOH, 0.5% NH4OH in dichloromethane

Sources & evidence

ORD record
ord-ca61494551de4c0ba48a86ba5066b8dc
Source dataset
uspto-grants-2009_02
Patent number
US07491737B2

Reaction notes

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