Diisopropylethylamine → 3-Chloro-5-(4-(4-methoxyphenethyl)piperazin-1-yl)-1,2,4-thiadiazole

HRID 570574Notes

Reaction equation

HRID 570574 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[Cl:19][C:20]1[N:24]=[C:23](Cl)[S:22][N:21]=1.CCN(C(C)C)C(C)C>CCO>[Cl:19][C:20]1[N:24]=[C:23]([N:14]2[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][C:8]3[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:18][CH:17]=3)[CH2:16][CH2:15]2)[S:22][N:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725055Dichloro-1,2,4-thiadiazoleHCID 12235718HCID 12235718, compound

Product 1

HCID 711872633-Chloro-5-(4-(4-methoxyphenethyl)piperazin-1-yl)-1,2,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-methoxyphenethyl)piperazine dihydrochloride (1.04 g, 3.55 mmol), 3,5-dichloro-1,2,4-thiadiazole (500 mg, 3.23 mmol) and DIPEA (1.33 g, 1.8 ml, 10.3 mmol) in 23 mL EtOH was stirred for 1 h at RT. The reaction solution was concentrated in vacuo and the crude product was purified by column chromatography on silica eluting with a gradient formed from heptane and EtOAc to yield, after evaporation of the product containing fraction, 1.06 g (97%) of the title compound as white solid. MS (m/e): 339.2 (MH+).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe crude product was purified by column chromatography on silica eluting with a gradient
  3. customformed from heptane and EtOAc
  4. customto yield
  5. customafter evaporation of the product
  6. additioncontaining fraction, 1.06 g (97%) of the title compound as white solid

Sources & evidence

ORD record
ord-f32cd801f0b3409daec3734ec21966aa
Source dataset
uspto-grants-2015_05
Patent number
US09023852B2

Reaction notes

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