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Synlett
Volumn , Issue 5, 2009, Pages 0751-0754
An efficient synthesis of N-arylputrescines and cadaverines
Author keywords

Alkylations; Amines; Cesium; Nitriles; Nitrogen
Indexed keywords

EID: 62349090239     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087817     Document Type: Article
Times cited : (10)
References (45)
  • 1
    • 0004139057 scopus 로고    scopus 로고
    • Oxford University Press: New York
    • (a) Cohen, S. S. A Guide to Polyamines; Oxford University Press: New York, 1998.
    • (1998) A Guide to Polyamines
    • Cohen, S.S.1
  • 6
    • 62349117461 scopus 로고    scopus 로고
    • US 6,872,852
    • (c) Burns, M. R. US 6,872,852, 2005.
    • (2005)
    • Burns, M.R.1
  • 32
    • 8644226086 scopus 로고    scopus 로고
    • (g) Fink, D. M. Synlett 2004, 13, 2394.
    • (2004) Synlett , vol.13 , pp. 2394
    • Fink, D.M.1
  • 43
    • 62349140720 scopus 로고    scopus 로고
    • Representative Procedure for the Synthesis of Compounds 2 A solution of 4-chlorobutyronitrile (2.5 mmol) in DMF (1 mL) was added during 1.5 h to a mixture of aniline (2.5 mmol, Cs2CO3 (2.5 mmol, and KI (5 mmol) in DMF (4 mL, The mixture was stirred 2.5 h at 95°C. After completion of the reaction, as indicated by TLC, the mixture was treated with Et2O (50 mL) and H2O (10 mL, The aqueous phase was separated and extracted with Et2O (30 mL, The combined organic layers were dried over anhyd Na2SO4 and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (SiO2, hexane-CHCl3) to furnish 4-(phenylamino)butyronitrile in 69% yield as an oil. Spectral and Analytical Data for Selected Compounds 4-(Phenylamino)butyronitrile (2a) was obtained as an oil (69, 1H NMR 300 MHz, CDCl3, δ, 7.17-7.2
    • 2: C, 75.82; H, 8.10; N, 16.08. Found: C, 75.76; H, 8.14; N, 16.10.
  • 45
    • 62349100862 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of Compounds 1 A solution of compound 2 (2 mmol) in THF (60 mL) was treated with with freshly generated borane. The solution was refluxed for 1 h, cooled, and treated with MeOH. The solvent was then eliminated in vacuo. The residue was refluxed with 10% HCl (60 mL, filtered and made alkaline with 10% aq NaOH. The alkaline mixture was extracted with CH2Cl2 (2 x 40 mL, The organic phase was washed with H2O (10 mL, dried over Na2SO 4, and filtered. The solvent was eliminated in vacuo. The crude product was purified by column chromatography (SiO2, CH 2Cl2-2-PrNH2, Spectral and Analytical Data for Selected Compounds N-Phenyl-1,4-butanediamine (1a) was obtained as an oil (80, 1H NMR (300 MHz, CDCl3, δ, 7.15-7.20 (2 H, m, 6.69 (1 H, tt, J, 7.3, 1.0 Hz, 6.60 2 H, td, J, 7
    • 2: C, 74.11; H, 10.18; N, 15.71. Found: C, 74.01; H, 10.21; N, 15.67. Spectral and analytical data of compounds 1b-h,j-l are available as Supporting Information.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.