Preparation of secondary amines by reductive amination with metallic magnesium
Апстракт
A novel and efficient method for the preparation of secondary amines by reductive amination of carbonyl compounds with primary amines has been developed, The reduction, effected with metallic magnesium in methanol, utilizing triethylamine-acetic acid as a buffer, gave pure secondary amines, mostly in good yields (65-80%). No formation of tertiary amines or alcohols was observed. Use of ammonium acetate as an amino component gave primary amines in modest yields (ca. 50%), together with variable amounts of secondary amines. Enamines failed to undergo reduction. The method is inexpensive, relatively rapid, operationally simple and suitable for large-scale preparations, In addition, a simple method for separation of primary amines from secondary ones has been developed.
Извор:
Journal of the Chemical Society. Perkin Transactions 1, 1996, 3, 265-269Издавач:
- Royal Soc Chemistry, Cambridge
DOI: 10.1039/p19960000265
ISSN: 0300-922X
WoS: A1996TU46300009
Scopus: 2-s2.0-0040023205
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Mićović, Ivan V. AU - Ivanović, Milovan AU - Roglić, Goran AU - Kiricojevic, VD AU - Popovic, JB PY - 1996 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2239 AB - A novel and efficient method for the preparation of secondary amines by reductive amination of carbonyl compounds with primary amines has been developed, The reduction, effected with metallic magnesium in methanol, utilizing triethylamine-acetic acid as a buffer, gave pure secondary amines, mostly in good yields (65-80%). No formation of tertiary amines or alcohols was observed. Use of ammonium acetate as an amino component gave primary amines in modest yields (ca. 50%), together with variable amounts of secondary amines. Enamines failed to undergo reduction. The method is inexpensive, relatively rapid, operationally simple and suitable for large-scale preparations, In addition, a simple method for separation of primary amines from secondary ones has been developed. PB - Royal Soc Chemistry, Cambridge T2 - Journal of the Chemical Society. Perkin Transactions 1 T1 - Preparation of secondary amines by reductive amination with metallic magnesium IS - 3 SP - 265 EP - 269 DO - 10.1039/p19960000265 ER -
@article{ author = "Mićović, Ivan V. and Ivanović, Milovan and Roglić, Goran and Kiricojevic, VD and Popovic, JB", year = "1996", abstract = "A novel and efficient method for the preparation of secondary amines by reductive amination of carbonyl compounds with primary amines has been developed, The reduction, effected with metallic magnesium in methanol, utilizing triethylamine-acetic acid as a buffer, gave pure secondary amines, mostly in good yields (65-80%). No formation of tertiary amines or alcohols was observed. Use of ammonium acetate as an amino component gave primary amines in modest yields (ca. 50%), together with variable amounts of secondary amines. Enamines failed to undergo reduction. The method is inexpensive, relatively rapid, operationally simple and suitable for large-scale preparations, In addition, a simple method for separation of primary amines from secondary ones has been developed.", publisher = "Royal Soc Chemistry, Cambridge", journal = "Journal of the Chemical Society. Perkin Transactions 1", title = "Preparation of secondary amines by reductive amination with metallic magnesium", number = "3", pages = "265-269", doi = "10.1039/p19960000265" }
Mićović, I. V., Ivanović, M., Roglić, G., Kiricojevic, V.,& Popovic, J.. (1996). Preparation of secondary amines by reductive amination with metallic magnesium. in Journal of the Chemical Society. Perkin Transactions 1 Royal Soc Chemistry, Cambridge.(3), 265-269. https://doi.org/10.1039/p19960000265
Mićović IV, Ivanović M, Roglić G, Kiricojevic V, Popovic J. Preparation of secondary amines by reductive amination with metallic magnesium. in Journal of the Chemical Society. Perkin Transactions 1. 1996;(3):265-269. doi:10.1039/p19960000265 .
Mićović, Ivan V., Ivanović, Milovan, Roglić, Goran, Kiricojevic, VD, Popovic, JB, "Preparation of secondary amines by reductive amination with metallic magnesium" in Journal of the Chemical Society. Perkin Transactions 1, no. 3 (1996):265-269, https://doi.org/10.1039/p19960000265 . .