Hydrochloric Acid → 1-[5-(3-Methyl-[1,2,4]-oxadiazol-5-yl)thiazol-2-yl]piperazine

HRID 1594009Notes

Reaction equation

HRID 1594009 reaction equation
Cl.[CH3:2][C:3]1[N:7]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)=[N:10][CH:9]=2)[O:5][N:4]=1>ClCCCl>[CH3:2][C:3]1[N:7]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:10][CH:9]=2)[O:5][N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69423493Tert-butyl 4-[5-(3-methyl-[1,2,4]-oxadiazol-5-yl)-thiazol-2-yl]piperazine-1-carboxylate

Product 1

HCID 685281391-[5-(3-Methyl-[1,2,4]-oxadiazol-5-yl)thiazol-2-yl]piperazineYield 96.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A satd ethanolic HCl soln (4 ml) was added to a solution of 220 mg (0.63 mmol) of tert-butyl 4-[5-(3-methyl-[1,2,4]-oxadiazol-5-yl)thiazol-2-yl]-piperazine-1-carboxylate [Precursor BBB62] in DCE (10 ml). After stirring at RT 5 min, the reaction solution was concentrated in vacuo. The residue was taken up in DCM and washed successively with a 1% strength aq. NaOH soln and water. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. 152 mg (0.61 mmol, 96%) of 1-[5-(3-methyl-[1,2,4]-oxadiazol-5-yl)thiazol-2-yl]piperazine were obtained here.

Workup

  1. concentrationthe reaction solution was concentrated in vacuo
  2. washwashed successively with a 1% strength aq. NaOH soln and water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1532c660678f43f788234b1dcb848902
Source dataset
uspto-grants-2007_11
Patent number
US07300939B2

Reaction notes

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