Ethylenediamine → 1-[2-Amino-4-(trifluoromethyl)phenyl]pyrrolidin-2-one

HRID 502760Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4].[NH:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18].C(N)CN.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.C1(C)C=CC=CC=1>[NH2:4][C:3]1[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:2]=1[N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A resealable tube was charged with 2-bromo-5-(trifluoromethyl)aniline (1.00 g, 4.16 mmol), 2-pyrrolidinone (0.425 g, 5.00 mmol), N,N′-ethylene diamine (0.037 g, 0.42 mmol), potassium carbonate (1.15 g, 8.32 mmol), copper iodide (0.80 mg, 0.42 mmol) and toluene (1.0 mL). The tube was sealed and the mixture was heated at 80° C. for 24 h. The resulting mixture was partitioned between ethyl acetate and water. The organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane) to afford 1-(2-amino-4-(trifluoromethyl)phenyl)pyrrolidin-2-one as a gray solid. MS m/z=245 [M+H]+. Calc'd for C11H11F3N2O: 244.

Workup

customThe tube was sealed
customThe resulting mixture was partitioned between ethyl acetate and water
customThe organic phase was separated
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane)

Sources & evidence

ORD record: ord-2cd0d031b196476493fe1db15da15114
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776869B2

Reaction notes

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