Propyne → 4-(Prop-1-yn-1-yl)aniline

HRID 734990ノート

反応式

HRID 734990 の反応式
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1CC[CH2:12][CH2:11][CH2:10]1.C#CC>[Cu]I.O>[C:10]([C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1)#[C:11][CH3:12]

参加物

6

反応物 3

HCID 6335PropyneHCID 8082PiperidineHCID 108934-Iodoaniline

生成物 1

HCID 450791534-(Prop-1-yn-1-yl)aniline

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒

実験手順

5.47 g (25 mmol) of 4-iodoaniline, 0.878 g (1.25 mmol) of bis-triphenylphosphine palladium dichloride, 0.47 g (2.5 mmol) of copper (I) iodide, and 20 mL of piperidine are placed in a pressure apparatus. Then 6.1 bar gaseous propyne are piped into the pressure apparatus, while the temperature rises to 39° C. It is therefore cooled with water. The mixture is stirred for 2 hours at ambient temperature and the reaction mixture is then extracted with ethyl acetate and water. The organic phase is dried over sodium sulfate, evaporated down, and the residue purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate (4:1)). Yield: 2.1 g (64% of theory); C9H9N (M=131.17); calc.: molecular ion peak (M+H)+: 132; found: molecular ion peak (M+H)+: 132.

後処理

  1. customrises to 39° C
  2. extractionthe reaction mixture is then extracted with ethyl acetate and water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated down
  5. customthe residue purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate (4:1))

出典と根拠

ORDレコード
ord-a2068621436141e9b50f77a25d47218f
出典データセット
uspto-grants-2009_09
特許番号
US07592373B2

反応ノート

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