Propyne → 4-(Prop-1-yn-1-yl)aniline

HRID 734990노트

반응식

HRID 734990 반응식
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]

참가 물질

6

반응물 3

HCID 6335PropyneHCID 8082PiperidineHCID 108934-Iodoaniline

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-a2068621436141e9b50f77a25d47218f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592373B2

반응 노트

불러오는 중…