Ammonium Hydroxide → HCID 178516745, compound

HRID 1762098Notes

Reaction equation

HRID 1762098 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]([N:21]1[CH2:26][CH2:25][C:24](=O)[CH:23]([C:28](OC)=O)[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-:32].[NH4+]>C(O)(=O)C>[CH2:14]([N:21]1[CH2:26][C:25](=[O:32])[C:24]2[N:1]=[C:2]3[N:3]=[C:4]([N:7]4[CH2:8][CH2:9][O:10][CH2:11][CH2:12]4)[NH:5][N:6]3[CH2:28][C:23]=2[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 107479Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochlorideHCID 44173793-morpholin-4-yl-1H-1,2,4-triazol-5-amine

Product 1

HCID 178516745HCID 178516745, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 50.76 g (0.3 mole) of 5-amino-3-morpholino-1H-1,2,4-triazole, 85.13 g (0.3 mole) of 1-benzyl-3-carbomethoxy-4-piperidone-hydrochloride and 175 ml of acetic acid is heated to boiling for 6 hours. After cooling 400 ml of concentrated ammonium hydroxide solution are added to the reaction mixture, which is then allowed to stand at room temperature for 16 hours. The precipitated crystals are filtered and washed with 200 ml of water. The product is heated to boiling in 500 ml of methanol for 15 minutes, filtered, washed with 400 ml of methanol, dissolved in hot dimethyl formamide, precipitated by adding acetonitrile, filtered and washed with acetonitrile. Thus 78.81 g of 7-benzyl-2-morpholino-6,7,8,9-tetrahydro-pyrido[4,3-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one are obtained, yield 72%, m.p.: 291°-293° C. The crystals precipitated from the methanol solution are filtered, washed with methanol, dissolved in 60 ml of hot dimethyl formamide, precipitated by adding 60 ml of acetonitrile, filtered and washed with acetonitrile. Thus 6.63 g of 7-benzyl-2-morpholino-6,7,8,9-tetrahydro-pyrido[4,3-d]-1,2,4-triazolo[1,5-a]pyrimidine-6(10H)-one are obtained, yield 6%, m.p.: 252°-254° C.

Workup

  1. temperatureis heated
  2. additionare added to the reaction mixture, which
  3. waitto stand at room temperature for 16 hours
  4. filtrationThe precipitated crystals are filtered
  5. washwashed with 200 ml of water
  6. temperatureThe product is heated
  7. waitto boiling in 500 ml of methanol for 15 minutes
  8. filtrationfiltered
  9. washwashed with 400 ml of methanol
  10. dissolutiondissolved in hot dimethyl formamide
  11. customprecipitated
  12. additionby adding acetonitrile
  13. filtrationfiltered
  14. washwashed with acetonitrile

Sources & evidence

ORD record
ord-5cb7f2412c014b9dafd0a467052e3d4b
Source dataset
uspto-grants-1989_05
Patent number
US04831029

Reaction notes

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