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Synthesis of local anesthetics

Schönenberger, Helmut, Vogel, H. and Bamann, E. (1965) Synthesis of local anesthetics. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 298 (6), pp. 371-378.

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The prepns. are described of the local anesthetic compds. MeO2CCH2CHRNHCHRCH2CH2OBz and the N-methyl derivs. 3-Amino-1-butanol (I), b11 63-5 Deg, was prepd. in 37.8% yield by dropwise addn. of a suspension of 28.5 g. LiAlH4 in 900 ml. abs. Et2O to an abs. Et2O soln. (500 ml.) of 0.4 mole methyl acetoacetate oxime (II), and stirring the gently boiling mixt. for 5 hrs. Me beta ...


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Item type:Article
Additional Information (public):CAN 63:45925 35 Noncondensed Aromatic Compounds 2704-50-9; 2704-58-7 (Derived from data in the 7th Collective Formula Index (1962-1966); 2704-56-5P Role: SPN (Synthetic preparation), PRP (Properties), PREP (Preparation) (Synthesis of local anesthetics); 2704-57-6 (Butyric acid, 3-[(3-hydroxy-1-methylpropyl)amino]-, methyl ester, benzoate (ester); 859038-85-0 (Butyric acid, 3-[(3-hydroxy-1-methylpropyl)methylamino]-, benzoate (ester) (as anesthetic); 2704-49-6P (Crotonic acid, 3-[(3-hydroxy-1-methylpropyl)amino]-, methyl ester); 2704-51-0P (Butyric acid, 3-(methylamino)-, methyl ester); 2704-55-4P (1-Butanol, 3-(methylamino)-); 2866-77-5P (Butyric acid, 3-[(3-hydroxy-1-methylpropyl)amino]-, methyl ester); 2867-59-6P (1-Butanol, 3-amino-); 2867-64-3P (1-Butanol, 3-chloro-, benzoate); 2867-65-4P (1,3-Butanediol, dibenzoate); 2867-66-5P (1-Butanol, 3-bromo-, benzoate); 2867-67-6P (1-Butanol, 3-bromo-, acetate); 856615-55-9P (Butyric acid, 3-[(3-hydroxy-1-methylpropyl)methylamino]-, acetate (ester) Role: PREP (Preparation) (prepn. of)
Institutions:Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Schönenberger
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Keywords:Anesthetics (3-[(3-hydroxy-1-methylpropyl)amino]butyric acid derivs. as local)
Dewey Decimal Classification:500 Science > 540 Chemistry & allied sciences
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Unknown
Item ID:18193
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