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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: | 291 | ||||
| Seitenbereich: | S. 373-375 | ||||
| Datum: | 1958 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 53:11596 10E Organic Chemistry: Benzene Derivatives 58496-40-5; 108263-68-9; 108263-69-0; 110938-27-7; 110939-19-0; 111586-41-5; 114910-46-2 (Derived from data in the 6th Collective Formula Index (1957-1961); 7025-95-8P; 7030-59-3P; 82165-21-7P; 94801-41-9P; 859438-22-5P; 1086223-97-3P; 1086233-33-1P; 1087400-07-4P; 1087401-40-8P; 1088227-83-1P; 1088227-91-1P; 1129271-40-4P Role: SPN (Synthetic preparation), PRP (Properties), PREP (Preparation) (Reduction of benzylidene alkylamines with activated aluminum in alcoholic solution); 7429-90-5 (Aluminum) (active, N-alkyl benzylidenimine redn. by); 102-97-6P (Benzylamine, N-isopropyl-); 103-49-1P (Dibenzylamine); 103-67-3P (Benzylamine, N-methyl-); 2032-33-9P (Benzylamine, N-propyl-); 2403-22-7P (Benzylamine, N-butyl-); 3647-71-0P (Phenethylamine, N-benzyl-); 4169-62-4P (Ethylenediamine, N,N'-dibutyl-1,2-diphenyl-); 4383-25-9P (Benzylamine, N-cyclohexyl-); 14321-27-8P (Benzylamine, N-ethyl-); 15018-21-0P (Ethylenediamine, N,N'-diethyl-1,2-diphenyl-); 22751-68-4P (Ethylenediamine, N,N'-dimethyl-1,2-diphenyl-); 22751-69-5P (Ethylenediamine, N,N'-dicyclohexyl-1,2-diphenyl-); 24431-19-4P (Ethylenediamine, N,N'-dibenzyl-1,2-diphenyl-); 55079-98-6P (Ethylenediamine, N,N'-diisopropyl-1,2-diphenyl-); 96504-88-0P (Ethylenediamine, N,N'-dibutyl-1,2-diphenyl-, dihydrochloride); 102599-97-3P (Ethylenediamine, 1,2-diphenyl-N,N'-dipropyl-); 103276-50-2P (Ethylenediamine, N,N'-diphenethyl-1,2-diphenyl-); 112247-77-5P (Ethylenediamine, N,N'-diisopropyl-1,2-diphenyl-, dihydrochloride); 112247-78-6P (Ethylenediamine, 1,2-diphenyl-N,N'-dipropyl-, dihydrochloride); 114159-65-8P (Ethylenediamine, N,N'-dicyclohexyl-1,2-diphenyl-, dihydrochloride); 115292-46-1P (Ethylenediamine, N,N'-dibenzyl-1,2-diphenyl-, dihydrochloride); 115294-01-4P (Ethylenediamine, N,N'-diphenethyl-1,2-diphenyl-, dihydrochloride); 131762-27-1P (Ethylenediamine, N,N'-diethyl-1,2-diphenyl-, dihydrochloride); 878794-82-2P (Ethylenediamine, N,N'-dimethyl-1,2-diphenyl-, dihydrochloride) Role: PREP (Preparation) (prepn. of); 622-29-7 (Methylamine, N-benzylidene-); 780-25-6 (Benzylamine, N-benzylidene-); 1077-18-5 (Butylamine, N-benzylidene-); 2211-66-7 (Cyclohexylamine, N-benzylidene-); 3240-95-7 (Phenethylamine, N-benzylidene-); 6852-54-6 (Ethylamine, N-benzylidene-); 6852-55-7 (Propylamine, N-benzylidene-); 6852-56-8 (Ethylamine, N-benzylidene-1-methyl-) (redn. of) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Entpflichtete oder im Ruhestand befindliche Professoren > Prof. Schönenberger | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | Amines (N-benzylidene, redn. of) | ||||
| 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: | 18201 |
Zusammenfassung
Dialkyldiphenylethylenediamines and benzylalkylamines were formed on reduction of benzylidenealkylamines with activated Al. Al foil (5.4 g.) and a little HgCl2. in 120 ml. EtOH warmed until H began to evolve, 0.1 mole Schiff base in 30 ml. C6H6 added, the mixt. heated 2 hrs. on the H2O bath, treated with 100 ml. C6H6 and 100 ml. 15% aq. NaOH, heated 15 min. more, 200 ml. H2O added, the mixt. ...
Zusammenfassung
Dialkyldiphenylethylenediamines and benzylalkylamines were formed on reduction of benzylidenealkylamines with activated Al. Al foil (5.4 g.) and a little HgCl2. in 120 ml. EtOH warmed until H began to evolve, 0.1 mole Schiff base in 30 ml. C6H6 added, the mixt. heated 2 hrs. on the H2O bath, treated with 100 ml. C6H6 and 100 ml. 15% aq. NaOH, heated 15 min. more, 200 ml. H2O added, the mixt. cooled, the C6H6 layer sepd., the aq. phase extd. 2-3 times with C6H6, the C6H6 solns. combined, dried, C6H6 removed, and the residue worked up as follows: (1) with Schiff bases with aliphatic groups on the N atom, the products were 1st distd. to obtain the amines, and the distn. residue taken up in Et2O, the soln. satd. with HCl gas, the ppt. sepd., and recrystd. to obtain the substituted diamines; (2) with PhCH:NBu (I), the C6H6 residue was distd. and the diamine isolated by conversion into their cryst. hydrochlorides; (3) with Schiff bases with aromatic and alicyclic groups on the N atom, the C6H6 residue was dissolved in as little warm MeOH as possible, the soln. kept 2 days in the refrigerator to obtain the substituted ethylenediamines, and the mother liquors distd. to obtain the amines. The following results were obtained (Schiff base used, g. amine formed, b.p./mm., g. ethylenediamine formed, m.p. given): PhCH:NMe, 1.8 PhCH2NHMe, 77-80 Deg/12, 8.7 PhMeNCH2CH2NPhMe.2HCl, 304 Deg (MeOH-Me2CO) [base, m. 135 Deg (petr. ether)]; PhCH: NEt, 2.1 PhCH2NHEt, 79-83 Deg/12, 11 PhEtNCH2CH2NPhEt.2HCl, 261 Deg (MeOHMe2CO) [base, m. 87-8 Deg (petr. ether)]; PhCH:NPr, 2.3 PhCH2NHPr, 102-8 Deg/12, 6.5 PhPrNCH2CH2NPhPr.2HCl, 205 Deg (MeOH-Et2O) [base, m. 83 Deg (petr. ether)]; PhCH: NCHMe2, 1.7 PhCH2NHCHMe2, 111-12 Deg/12, 5.9 Ph(Me2CH)NCH2CH2NPh(CHMe2).2HCl, 250 Deg (MeOH-Me2CO) [base, m. 119 Deg (petr. ether)]; I, 4.3 PhCH2NHBu, 115-20 Deg/12, 8.1 PhBuNCH2CH2NPhBu.2HCl, 185-220 Deg (MeOH-Et2O) (base, b0.5 158-70 Deg); PhCH:NCH2Ph2, 7.4 (PhCH2)2NH, 114 Deg/0.03, Ph(PhCH2)NCH2CH2Ph(CH2Ph).2HCl, 235-8 Deg (MeOH-Et2O) [base, m. 151 Deg (MeOH)]; PhCH:NCH2CH2Ph, 6.4 PhCH2NHCH2CH2Ph, 122-5 Deg/ 0.03, 9.6 [Ph(PhCH2CH2)NCH2]2.2HCl, 239-40 Deg (MeOHEt2O) [base, m. 123 Deg (MeOH); PhCH:NR (R = cyclohexyl), 2.0 PhCH2NHR, 75-8 Deg/0.03, 13.9 PhRNCH2CH2NPhR.2HCl, 261-3 Deg (MeOH-Et2O) [base, m. 128 Deg (MeOH)].
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