Triethylamine → N-[3-[3-(1-Piperidinylmethyl)phenoxy]propyl]-1,3,4-thiadiazole-2,5-diamine

HRID 649134Notes

Reaction equation

HRID 649134 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[O:11][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:20]([CH2:23]C)CC)C.BrC1[S:30][C:29]([NH2:31])=[N:28][N:27]=1>C1COCC1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:31][C:29]2[S:30][C:23]([NH2:20])=[N:27][N:28]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 36508832-Amino-5-bromo-1,3,4-thiadiazoleHCID 19804246HCID 19804246, compound

Product 1

HCID 13541111N-[3-[3-(1-Piperidinylmethyl)phenoxy]propyl]-1,3,4-thiadiazole-2,5-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.57 g (2.3 mmol) of 1-Amino-[3-[3-(1-piperidinomethyl)phenoxy]-propane, 0.35 ml of triethylamine and 0.42 g (2,3 mmol) of 5-bromo-1,3,4-thiadiazole-2-amine are heated under reflux in 20 ml of THF for 3 hours. Solid triethylammonium bromide is filtered off, the filtrate is concentrated by evaporation and the residue is purified by preparative layer chromatography.

Workup

  1. filtrationSolid triethylammonium bromide is filtered off
  2. concentrationthe filtrate is concentrated by evaporation
  3. customthe residue is purified by preparative layer chromatography

Sources & evidence

ORD record
ord-23ac849ad05746278524037b3d8a1357
Source dataset
uspto-grants-1988_04
Patent number
US04738960

Reaction notes

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