Hydrochloric Acid → 5-(2-Piperazin-1-ylethyl)-2,1,3-benzoxadiazole

HRID 1519503Notes

Reaction equation

HRID 1519503 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH:7]=[CH:6][C:5]=12.Cl>O1CCOCC1>[N:12]1([CH2:11][CH2:10][C:8]2[CH:7]=[CH:6][C:5]3=[N:1][O:2][N:3]=[C:4]3[CH:9]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66646566Tert-butyl 4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazine-1-carboxylate

Product 1

HCID 151663825-(2-Piperazin-1-ylethyl)-2,1,3-benzoxadiazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl 4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazine-1-carboxylate (470 mg, 1.4 mmol) was then dissolved in dioxane (10 mL) and added 7 mL of 4M HCl in dioxane. The reaction was stirred at room temperature overnight. Evaporated off all solvent and the residue was taken up in ethyl acetate basified with 1N NaOH. The ethyl acetate was separated and washed with brine then dried over Na2SO4 and evaporated to dryness. The residue was purified by chromatography using 5% (NH4OH:MeOH 1:10) in 95% DCM to yield 5-(2-piperazin-1-ylethyl)-2,1,3-benzoxadiazole. 1H-NMR (600 MHz, CDCl3): δ 7.72 (d, J=9.2 Hz, 1H), 7.28 (d, J=9.2 Hz, 1H), 2.92 (t, J=4.9 Hz, 2H), 2.88 (t, J=7.6 Hz, 1H), 2.65 (t, J=7.6 Hz, 1H). LC-MS: M+1=233.

Workup

  1. customEvaporated off all solvent
  2. customThe ethyl acetate was separated
  3. washwashed with brine
  4. dry with materialthen dried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-02749bc007e74dbea5088a57667fe333
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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