Synthesis of 2-[2-(3,4,5-Trimethoxybenzoyloxy)ethyl]pyrrolidine Hydrochloride Controlled by GC-MS, 1H and 13C NMR Analyses

The synthesis of 2-[2-(3,4,5-trimethoxybenzoyloxy)ethyl]pyrrolidine hydrochloride was performed using 2-(2-hydroxyethyl)pyrrolidine as a starting material. Before the O-acylation reaction with 3,4,5-trimethoxybenzoyl chloride, the amino group was protected using benzyl chlorocarbonate. The removal of the blocking group was carried out in modified conditions, avoiding the alcoholysis of the ester bond. The final product was separated from its structural isomer by precipitation as its hydrochloride salt. Some steps of the synthesis were controlled by GC-MS. The identification of the respective compounds was performed by mass spectra analyses and confirmed by 1H NMR, 13C NMR, IR and elemental analyses.

Synthesis of 2-[2-(3,4,5-Trimethoxybenzoyloxy)ethyl]pyrrolidine Hydrochloride Controlled by GC-MS, 1H and 13C NMR Analyses

The synthesis of 2-[2-(3,4,5-trimethoxybenzoyloxy)ethyl]pyrrolidine hydrochloride was performed using 2-(2-hydroxyethyl)pyrrolidine as a starting material. Before the O-acylation reaction with 3,4,5-trimethoxybenzoyl chloride, the amino group was protected using benzyl chlorocarbonate. The removal of the blocking group was carried out in modified conditions, avoiding the alcoholysis of the ester bond. The final product was separated from its structural isomer by precipitation as its hydrochloride salt. Some steps of the synthesis were controlled by GC-MS. The identification of the respective compounds was performed by mass spectra analyses and confirmed by 1H NMR, 13C NMR, IR and elemental analyses.

___

  • J.S. Glasby, “Encyclopedia of the Alkaloids”, Vol. 1, pp. 185, 730, Plenum Press, New York and London, P.W. Meerstadt, Br. Med. J. (Clin. Res. Ed.)., 285(6336), 196-7 (1982).
  • H. Yeager Jr, R.M. Weinberg, L.V. Kaufman and S. Katz, J. Clin. Pharmacol. 16, 198-207 (1976).
  • A. Dutkiewicz, E. Bobrowska and A. Milczarek, Polish Pat. 100410 (1979).
  • J. W. Slater, A.D. Zechnich and D.G. Haxby, Drugs 57, 31-47 (1999).
  • W. Beckschafer, Arzneimittelforschung 18, 1079-80 (1968).
  • M. Eckstein and E. Herdegen, Pol. J. Pharmacol. Pharm. 32, 817-821 (1980).
  • T. Gohda, Y. Makita, T. Shike, K. Funabiki, J. Shirato and Y. Tomino, Kidney Blood Press Res. 24, 33-38 (2001).
  • R. Dobrzeniecka and A. Zie˜nkowicz, Organika – Researches of the Institute of Industrial Organic Chemistry (in Polish) 1999-2000, 59-63.
  • B. Weiss, J. Am. Chem. Soc. 79, 5553-5 (1957).
  • H. Kimura and Ch.H. Stammer, J. Org. Chem. 48, 2440-1 (1983).
  • J. Fuhrhop and G. Penzil, “Organic Synthesis. Concepts, Methods, Starting Materials“, pp. 146-148, Verlag Chemie GmbH, Weinheim, 1983.
  • T. Wr´obel (Ed.), Preparation and Elements of the Organic Synthesis (in Polish), pp. 805, PWN, Warsaw, 1983.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Heterogeneous Electron Transfer Rate Constants of Viologen at a Platinum Disk Electrode

Naheed Kaukab BHATTI, M. Sadiq SUBHANI, Ather Yaseen KHAN

Spectrophotometric Study of the Interaction Between Aza-15-Crown-5 and Some p-Acceptors in Chloroform Solution

Hamid Reza POURETEDAL, Abolfazl SEMNANI

Extraction-Spectrophotometric Determination of Trace Amounts of Barium and Strontium by 18-Crown-6 and Rose Bengal Using Partial Least Squares

Jahanbakhsh GHASEMI

Interpretation of Sorption Kinetics for Mixtures of Reactive Dyes on Wool

Elif ŞAHİN

Synthesis of 2-[2-(3,4,5-Trimethoxybenzoyloxy)ethyl]pyrrolidine Hydrochloride Controlled by GC-MS, 1H and 13C NMR Analyses

Alicja WODNICKA, Maygorzata DZIECIOL

A New Approach Towards (\pm)-4-Ipomeanol and Its 2-Furyl Regioisomer

Jürgen KRAUSS, Franz BRACHER and Doris UNTERREITMEIER

Construction and Characterization of Indium Liquid Ion Selective Electrodes Based on Crown Ethers in a PVC Matrix Membrane

Najwa I. ABDULLA, Abdul-Muhsin Al--HAIDER

Investigation of Electron Transfer Reaction Between Diphenylbenzidine and Ascorbic Acid

Iftikhar Imam NAQVI, Abida PERVEEN

Reactions of Alkenes with Sodium Perborate and Sodium Chloride

Erdal ŞENOCAK, Yavuz TAŞKESENLİGİL Ferhan TÜMER, Cavit KAZAZ, Ferhan TÜMER

Characterization of $TiO_2$ synthesized in alcohol by a sol-gel process: The effects of annealing temperature and acid catalyst

Ertuğrul ARPAÇ, Murat AKARSU, Meltem ASİLTÜRK, Yunus ÖNAL, Hikmet SAYILKAN, Funda SAYILKAN