Acetic Acid → HCID 178517719, compound

HRID 1762101Notes

Reaction equation

HRID 1762101 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[N:3]=1.Cl.[CH2:14](N1CCC(C(OCC)=O)C(=O)C1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:33]([OH:36])(=O)[CH3:34].[N:37]1C=[CH:41][CH:40]=[CH:39][CH:38]=1>O.CC(C)=O>[CH2:14]([CH:39]1[C:40]2[CH2:41][N:6]3[NH:5][C:4]([N:7]4[CH2:8][CH2:9][O:10][CH2:11][CH2:12]4)=[N:3][C:2]3=[N:1][C:34]=2[C:33](=[O:36])[NH:37][CH2:38]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1049Pyridine2×HCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochlorideHCID 44173793-morpholin-4-yl-1H-1,2,4-triazol-5-amine

Product 1

HCID 178517719HCID 178517719, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 50.8 g (0.3 mole) of 5-amino-3-morpholino-1H-1,2,4-triazole, 89.3 g (0.3 mole) of 1-benzyl-4-carbethoxy-3-oxo-piperidine-hydrochloride and 220 ml of acetic acid is refluxed for 7 hours under stirring. The reaction mixture is allowed to stand overnight, the precipitate is filtered and washed with acetone. The product thus obtained is dissolved in a mixture of 400 ml of water and 100 ml of pyridine under heating to boiling for 15 minutes. The solution is allowed to stand for a day, the precipitated crystals are filtered and washed with acetone. The product thus obtained (83.9 g) is dissolved in 260 ml of hot pyridine, to the solution 1000 ml of acetone are added. The precipitated crystals are filtered and washed with acetone. Thus 78.9 g of the desired compound are obtained, yield 72%, m.p.: 315°-317° C.

Workup

  1. temperatureis refluxed for 7 hours
  2. filtrationthe precipitate is filtered
  3. washwashed with acetone
  4. customThe product thus obtained
  5. temperatureunder heating
  6. waitto boiling for 15 minutes
  7. waitto stand for a day
  8. filtrationthe precipitated crystals are filtered
  9. washwashed with acetone
  10. customThe product thus obtained (83.9 g)
  11. additionare added
  12. filtrationThe precipitated crystals are filtered
  13. washwashed with acetone

Sources & evidence

ORD record
ord-d442ff68ea8a4507bac7f54d43aa8b86
Source dataset
uspto-grants-1989_05
Patent number
US04831029

Reaction notes

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