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

HRID 502760

反応式

HRID 502760 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2cd0d031b196476493fe1db15da15114
出典データセット
uspto-grants-2010_08
特許番号
US07776869B2

関連ノート

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