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

HRID 502760

반응식

HRID 502760 반응식
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]

참가 물질

7

반응물 4

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 679892-Bromo-5-(trifluoromethyl)benzenamine

생성물 1

HCID 167867611-[2-Amino-4-(trifluoromethyl)phenyl]pyrrolidin-2-one

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2cd0d031b196476493fe1db15da15114
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776869B2

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