Hydrochloric Acid → 1-[2-(4-Nitrophenyl)ethyl]piperazin-2-one

HRID 1466007Notes

Reaction equation

C(OC([N:8]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[CH2:9][CH2:10][NH:11][CH2:12][C:13](OCC)=[O:14])=O)(C)(C)C.Cl.C(N(CC)CC)C>O1CCOCC1>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][N:8]2[CH2:9][CH2:10][NH:11][CH2:12][C:13]2=[O:14])=[CH:21][CH:22]=1)([O-:28])=[O:27]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of Ethyl [(2-{(tert-butoxycarbonyl) [2-(4-nitrophenyl)ethyl]amino}ethyl)amino]acetate (0.50 g, 1.3 mmol) in dioxane (4 mL) was added 4N HCl in dioxane (3.2 mL, 13 mmol). The solution was stirred at 25° C. for 2 hours. LC showed complete removal of the Boc group. The volatiles were removed under vacuum, and the residue was redissolved in toluene and ethanol. To that solution was added triethylamine (0.73 mL, 5.2 mmol). The mixture was heated to reflux for 48 hours. LC at that point showed mostly product. The product was purified by silica gel chromatography (DCM: MeOH) to afford 1-[2-(4-nitrophenyl)ethyl]piperazin-2-one. LC-MS (IE, m/z): 250 [M+1]+.

Workup

customremoval of the Boc group
customThe volatiles were removed under vacuum
dissolutionthe residue was redissolved in toluene
temperatureThe mixture was heated
temperatureto reflux for 48 hours
customThe product was purified by silica gel chromatography (DCM: MeOH)

Sources & evidence

ORD record: ord-b193a0d2ef2e4f1cb2385cea30a915a1
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999990B2

Reaction notes

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