Hydrochloric Acid → 1-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazine

HRID 2263365Notes

Reaction equation

HRID 2263365 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CCCCCC>C(OCC)(=O)C>[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 66523705Tert-butyl 4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxylate

Product 1

HCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl 4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxylate (5.06 g, 14.6 mmol) in ethyl acetate (80 ml) was added a 4 N solution of hydrogen chloride in ethyl acetate (40 ml), and the mixture was stirred at room temperature for 5 hours. Hexane (200 ml) was added to the reaction mixture and a precipitated solid was collected by filtration. The obtained solid was added to an aqueous saturated sodium bicarbonate solution (300 ml), followed by stirring at room temperature for 2 hours. The obtained powder was collected by filtration to yield 2.77 g (77.0%) the desired product.

Workup

  1. filtrationa precipitated solid was collected by filtration
  2. additionThe obtained solid was added to an aqueous saturated sodium bicarbonate solution (300 ml)
  3. stirringby stirring at room temperature for 2 hours
  4. filtrationThe obtained powder was collected by filtration

Sources & evidence

ORD record
ord-428d211896b54f819249738a403ad34c
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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