Ammonium Hydroxide → HCID 178483023, compound

HRID 1762099Notes

Reaction equation

HRID 1762099 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([N:7]([CH3:9])[CH3:8])[N:3]=1.Cl.[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH:20]([C:25](OC)=O)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-:29].[NH4+]>C(O)(=O)C>[CH2:11]([N:18]1[CH2:23][C:22](=[O:29])[C:21]2[N:1]=[C:2]3[N:3]=[C:4]([N:7]([CH3:9])[CH3:8])[NH:5][N:6]3[CH2:25][C:20]=2[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 107479Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochlorideHCID 3079781H-1,2,4-Triazole-3,5-diamine, N,N-dimethyl-

Product 1

HCID 178483023HCID 178483023, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5.09 g (0.04 mole) of 5-amino-3-dimethylamino-1H-1,2,4-triazole, 11.35 g (0.04 mole) of 1-benzyl-3-carbomethoxy-4-piperidone-hydrochloride and 40 ml of acetic acid is heated to boiling for 2 hours. The reaction mixture is allowed to stand at room temperature for 16 hours. To the mixture 70 ml of a 25% ammonium hydroxide solution are added, the precipitated crystals are filtered and washed with hot methanol. The product is heated to boiling with 20 ml of methanol for 10 minutes and filtered again. The crystals are dried and dissolved in hot dimethyl formamide. The product is precipitated by adding acetonitrile, filtered and washed with acetone. Thus 12.179 g of 7-benzyl-2-dimethylamino-6,7,8,9-tetrahydro-pyrido[4,3-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one are obtained, yield 58%, m.p.: 279°-281° C.

Workup

  1. temperatureis heated
  2. waitto stand at room temperature for 16 hours
  3. filtrationthe precipitated crystals are filtered
  4. washwashed with hot methanol
  5. temperatureThe product is heated
  6. waitto boiling with 20 ml of methanol for 10 minutes
  7. filtrationfiltered again
  8. customThe crystals are dried
  9. dissolutiondissolved in hot dimethyl formamide
  10. customThe product is precipitated
  11. additionby adding acetonitrile
  12. filtrationfiltered
  13. washwashed with acetone

Sources & evidence

ORD record
ord-293a30bdd11046dba4eb054b4f9b4694
Source dataset
uspto-grants-1989_05
Patent number
US04831029

Reaction notes

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