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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft | ||||
| Verlag: | Verl. Chemie | ||||
| Band: | 298 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 6 | ||||
| Seitenbereich: | S. 367-371 | ||||
| Datum: | 1965 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 63:31027 32 Physical Organic Chemistry 2403-22-7P (Benzylamine, N-butyl-) Role: PREP (Preparation) (formation from N-benzylidenebutylamine and isopropylmagnesium halides, in N-benzylidenebutylamine redn. with Al-Hg); 544-40-1 (Butyl sulfide) (hydrogenolysis of, solvent effect in); 1165-52-2P (Ethylenediamine, N,N'-dibutyl-1,2-diphenyl-, meso-); 4169-62-4P (Ethylenediamine, N,N'-dibutyl-1,2-diphenyl-, (-)-) Role: PREP (Preparation) (prepn. of); 1077-18-5 (Butylamine, N-benzylidene-) (redn. of, by Al-Hg); 7439-97-6 (Mercury) (N-benzylidenebutylamine redn. by Al and); 7429-90-5 (Aluminum) (N-benzylidenebutylamine redn. by Hg and) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Entpflichtete oder im Ruhestand befindliche Professoren > Prof. Schönenberger | ||||
| Identifikationsnummer: |
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| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status: | Veröffentlicht | ||||
| Begutachtet: | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden: | Unbekannt / Keine Angabe | ||||
| Dokumenten-ID: | 18187 |
Zusammenfassung
cf. Schoenenberger, et al., CA 62, 6992f, 7664a, 13163g. The mechanism of redn. was investigated of benzylidenealkyl- and benzylidenearylamine-type Schiff bases with activated Al, to form mono- and dimeric secondary amines. Redn. of PhCH:NBu (I) in abs. EtOH with Al-Hg gave yields of benzylbutylamine (II) and N,N'-dibutyl-alpha ,alpha '-diphenylethylenediamine (III) (in meso- and racemic forms) ...
Zusammenfassung
cf. Schoenenberger, et al., CA 62, 6992f, 7664a, 13163g. The mechanism of redn. was investigated of benzylidenealkyl- and benzylidenearylamine-type Schiff bases with activated Al, to form mono- and dimeric secondary amines. Redn. of PhCH:NBu (I) in abs. EtOH with Al-Hg gave yields of benzylbutylamine (II) and N,N'-dibutyl-alpha ,alpha '-diphenylethylenediamine (III) (in meso- and racemic forms) which varied with the amt. of EtOH. HgCl2 (200 mg.) was dissolved in abs. EtOH (12.5-400 ml.), the soln. heated to boiling (78 Deg) under reflux, and 2 g. Al foil (0.1 mm. thick) added. After 5 min., 4 g. I in 20 ml. abs. EtOH was added to the 78 Deg mixt. with vigorous stirring. The reaction was continued at 78 Deg until the metals dissolved (.apprx.2 hrs.). Concd. HCl (40 ml.) was added to the gelatinous mixt.; the soln. was evapd. almost to dryness on a 100 Deg bath. The green residue was mixed with small vols. of 30% NaOH until the soln. was alk.; the mixt. was extd. with an equal vol. of CHCl3 (3 times), and the combined CHCl3 exts. dried over anhyd. Na2SO4. The dried CHCl3 soln. was satd. with HCl gas, and the CHCl3 distd. The residue (mainly II.HCl + III.HCl) was extd. in a Craig 34 stage countercurrent extn. app., using 40:12:28 CHCl3-MeOH-2% HCl solvent. The compn., and no., of the sepd. fractions are: (A) racemic III, 1-5; (B) meso-III, 6-21; (C) II, 22-34, resp. The av. yields of II, racemic III and meso-III, using first vols. of 12.5, 25, 50, 100, 200, 300, and 400 ml. of abs. EtOH in the redns. of I, are 10.0, 45.1, 45.4; 15.9, 41.5, 42.7; 27.2, 36.1, 36.8; 41.0, 29.0, 30.1; 59.0, 20.2, 20.8; 67.9, 15.7, 16.4; and 71.9, 13.3, 14.9%, resp. Cf. Arzneimittel-Forsch, 15(1), 30-6(1965).
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