Formylation of Secondary Amines with Dimethylformamide Dimethylacetal
- 1 January 1980
- journal article
- research article
- Published by Taylor & Francis in Analytical Letters
- Vol. 13 (9) , 759-769
- https://doi.org/10.1080/00032718008077997
Abstract
Secondary amines are formylated by dimethylformamide dimethylacetal, contradicting recent reports on the ethylation of secondary amines by this reagent. This explains why a single derivative is obtained regardless of the alkyl acetal that is used. These formyl derivatives, also formed by reaction with formic acid, are eluted later than the starting material or the corresponding ethyl derivative. Deuterated imipramine and related antidepressants can be prepared by reducing the formyl derivative of the appropriate desalkyl compound with lithium aluminum deuteride.Keywords
This publication has 11 references indexed in Scilit:
- N-Alkylation of Secondary Amine Tricyclic Antidepressants as a General Method for Their Quantitation by GC-MS-SIM Technique. Preparation of N-Ethyl Derivatives of Desimipramine, Nortriptyline, Protiptyline and DesmethyldoxepinAnalytical Letters, 1979
- A Precautionary Note Regarding Derivatization of Secondary Amines with Dialkylacetals of Formamide Other Than the Diethyl DerivativeAnalytical Letters, 1979
- Gas-liquid chromatographic determination of carbamazepine and phenylethylmalonamide in plasma after reaction with dimethylformamide dimethylacetalJournal of Chromatography B: Biomedical Sciences and Applications, 1978
- N-dimethylaminomethylene derivatives for the gas-liquid chromatography of primary sulfonamidesJournal of Chromatography A, 1975
- A Rapid Gas Chromatographic Analysis of Diastereomeric DiaminesJournal of Chromatographic Science, 1975
- Amino Acid N-Dimethylaminomethylene Alkyl Esters. New Derivatives for GC and GC-MS StudiesAnalytical Letters, 1972
- Die Reaktion von Carbonsäuren mit Acetalen des N, N‐Dimethylformamids: eine VeresterungsmethodeHelvetica Chimica Acta, 1965
- Säureamid‐Reaktionen, XXXVIII. Umsetzungen von Kohlensäurederivaten und Aminen mit Formylierungsmitteln: Synthesen disubstituierter s‐Triazine und trisubstituierter FormamidineEuropean Journal of Inorganic Chemistry, 1964
- Die Reaktion von Carbonsäuren und Phenolen mit AmidacetalenAngewandte Chemie, 1963
- Über Säureamidacetale, Harnstoffacetale und LactamacetaleEuropean Journal of Organic Chemistry, 1961