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- W1951360064 abstract "N,N-Dimethylanilin (4) und N-Methylen-morpholiniumchlorid (10g) reagieren über 4-Morpholinomethyl-N,N-dimethylanilin (9g) zu 2,4-Bis(morpholinomethyl)-N,N-dimethylanilin (11g). Aus 4-Dimethylaminomethyl- oder 4-Pyrrolidinomethyl-N,N-dimethylanilin (9a bzw. 9e) und allen eingesetzten Dialkylmethyleniminiumchloriden 10 entstehen hingegen keine zweifach im Kern aminomethylierten Produkte 11 sondern die Quartärsalze 12. N-Chlormethyl-benzamid (13a) oder N-Chlormethyl-N-methylbenzamid (13b) reagieren mit N,N-Dimethylanilin zu einem Gemisch der Monoamidomethylierungsprodukte in o- bzw. p-Stellung 14 bzw. 15 und den o,p-disubstituierten Verbindungen 16. Mit dem phenylogen Aminal 9a setzen sich 13a und 13b nicht unter Kernsubstitution sondern zu den Quartärsalzen 17 um. Amino- and Amidomethylation of N,N-Dimethylaniline and Related Derivatives The reaction of N,N-dimethylaniline (4) with N-methylenemorpholinium chloride (10g) affords 2,4-bis(morpholinomethyl)-N,N-dimethylaniline (11g) via 4-(morpholinomethyl)-N,N-dimethylaniline (9g) as an intermediate. From 4-(dimethylaminomethyl)- or 4-(pyrrolidinomethyl)-N,N-dimethylaniline (9a and 9e) and all dialkyl(methylene)iminium chlorides 10 so far used the quaternary salts 12 are formed, rather than the products 11, which are aminomethylated twice at the aromatic nucleus. N-Chloromethylbenzamide (13a) or N-chloromethyl-N-methylbenzamide (13b) are shown to undergo reaction with N,N-dimethylaniline to form a mixture of the monoamidomethylation products 14 and 15 substituted in o- and p-position, resp., in addition to o,p-disubstituted compounds of type 16. Upon treatment of 13a and 13b with the phenylogous aminal 9a instead of ring substitution amidoalkylation to quaternary salts of type 17 takes place." @default.
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- W1951360064 date "1982-01-01" @default.
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- W1951360064 title "Zur Amino- und Amidomethylierung vonN,N-Dimethylanilin und Abkömmlingen" @default.
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- W1951360064 doi "https://doi.org/10.1002/ardp.19823150110" @default.
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