3-[4-(1-Piperidinylmethyl)phenoxy]-1-propanamine → 1-Methyl-3-(methylthio)methyl-N-[3-[4-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-5-amine

HRID 652105Notes

Reaction equation

HRID 652105 reaction equation
[CH3:1][S:2][CH2:3][C:4]([N:6]=[C:7]([N:10]([CH3:19])[N:11]=CC1C=CC=CC=1)SC)=O.[N:20]1([CH2:26][C:27]2[CH:37]=[CH:36][C:30]([O:31][CH2:32][CH2:33][CH2:34][NH2:35])=[CH:29][CH:28]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1.Cl>[CH3:19][N:10]1[C:7]([NH:35][CH2:34][CH2:33][CH2:32][O:31][C:30]2[CH:36]=[CH:37][C:27]([CH2:26][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:28][CH:29]=2)=[N:6][C:4]([CH2:3][S:2][CH3:1])=[N:11]1

Participants

5

Reactant 2

HCID 140865533-[4-(1-Piperidinylmethyl)phenoxy]-1-propanamineHCID 53810570Methyl N-[2-(methylthio)acetyl]-1-methyl-2-(phenylmethylene)hydrazine carboximidothioate

Product 1

HCID 201991621-Methyl-3-(methylthio)methyl-N-[3-[4-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-5-amineYield 73.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Procedure

Methyl N-[2-(methylthio)acetyl]-1-methyl-2-(phenylmethylene)hydrazine carboximidothioate (1.2 g) and 3-[4-(1-piperidinylmethyl)phenoxy]propanamine (0.9 g) were heated at 55° under water vacuum for 2 h. Additional carboximidothioate (0.09 g) was then added and the mixture heated for a further 1 h. The reaction mixture was dissolved in toluene (5 ml) and 5N hydrochloric acid (4 ml), stirred at room temperature for 18 h and the phases separated. The aqueous phase was basified to pH 10 with sodium carbonate and extracted with ethyl acetate to give an oil, which was chromatographed using ethyl acetate-methanol (3:1) to give the title compound (1.04 g) as an orange brown oil.

Workup

  1. additionAdditional carboximidothioate (0.09 g) was then added
  2. temperaturethe mixture heated for a further 1 h
  3. customthe phases separated
  4. extractionextracted with ethyl acetate
  5. customto give an oil, which
  6. customwas chromatographed

Sources & evidence

ORD record
ord-b265223291b749da8093131a9ecb42b6
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Reaction notes

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