Water → tert-Butyl 4-[3-(3-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxylate

HRID 2263025Notes

Reaction equation

HRID 2263025 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:11]=[CH:10][S:9][CH:8]=2)[N:3]=1.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C.O>CN(C)C=O>[S:9]1[CH:10]=[CH:11][C:7]([C:4]2[N:3]=[C:2]([N:15]3[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]3)[S:6][N:5]=2)=[CH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 538814275-Chloro-3-(3-thienyl)-1,2,4-thiadiazole

Product 1

HCID 68778008tert-Butyl 4-[3-(3-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-3-(3-thienyl)-1,2,4-thiadiazole (2.47 g, 12.2 mmol) and tert-butyl piperazine-1-carboxylate (2.27 g, 12.2 mmol) in dimethylformamide (25 ml) was added triethylamine (6.8 ml, 48.8 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=9:1) to give 3.72 g (86.5%) of the desired product as a solid.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=9:1)

Sources & evidence

ORD record
ord-a1900776fb0d4ca396e82552dceb5b94
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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