Hydrochloric Acid → 1-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]-2-piperazinone

HRID 1466012Notes

Reaction equation

C(OC([N:8]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=O)=[CH:22][CH:21]=1)[CH2:9][CH2:10][NH:11][CH2:12][C:13](OCC)=[O:14])=O)(C)(C)C.Cl.O1CCOCC1.CC[N:38](C(C)C)C(C)C>>[N:26]1[O:28][N:38]=[C:24]2[CH:25]=[C:20]([CH2:19][CH2:18][N:8]3[CH2:9][CH2:10][NH:11][CH2:12][C:13]3=[O:14])[CH:21]=[CH:22][C:23]=12

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 81531Diisopropylethylamine

HCID 131732667Ethyl [(2-{(tert-butoxycarbonyl) [2-(4-nitrophenyl)ethyl]amino}ethyl)amino]acetate

Product 1

HCID 895261841-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]-2-piperazinone

Conditions

Temperature: 120 °C

Procedure

To a flask charged with ethyl [(2-{(tert-butoxycarbonyl)[2-(4-nitrophenyl)ethyl]amino}ethyl)amino]acetate (500 mg, 1.3 mmol) and a stir bar was added 4N HCl in dioxane (3.2 mL, 13 mmol). When LC indicated the reaction was done, solvents were removed under reduced pressure. The resulting residue was dissolved in ethanol (20 mL), and Hunig's base (1.1 mL, 6.4 mmol) was added to the solution. The reaction was heated to 120° C. for 16 hours. LC showed formation of the desired product, which was purified by silica gel chromatography to provide 1-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]piperazin-2-one. LC-MS (IE, m/z): 247 [M+1]+.

Workup

customsolvents were removed under reduced pressure
dissolutionThe resulting residue was dissolved in ethanol (20 mL)

Sources & evidence

ORD record: ord-b6054f75a6c146c69182a673a77534da
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999990B2

Reaction notes

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