N,N-Dicyclohexylmethylamine is used as a reagent in the base preparation of 13C2- and 2H phenethylamines as internal standards for IDMS by Pd-catalyzed double carbonylation of aryl iodides in the presence of amine nucleophiles followed by deoxygenation.
N,N-Dicyclohexylmethylamine has been employed as:
- catalyst during O-phenylation of tertiary alcohol with organobismuth(V) compounds
- base during Pd-catalyzed 5-endo-trig cyclization of 1-(o-bromophenyl)-2-methylprop-2-en-1-ol
ChEBI: N-Cyclohexyl-N-methylcyclohexanamine is an amine.
N,N-Dicyclohexylmethylamine has uses similar to those of the other cyclohexylamines, e.g., as a urethane foam catalyst.
N,N-Dicyclohexylmethylamine is prepared by methylating dicyclohexylamine
with dimethyl sulfate or by the
Leuckart – Wallach reaction.
The general procedure for the synthesis of N-methyldicyclohexylamine from the compound (CAS:88374-60-1) is as follows: phenylboronic acid (1.0 equiv. for aliphatic N-oxides and 1.5 equiv. for pyridine N-oxides) was mixed with tertiary amine N-oxide (1 mmol) in dichloroethane (2 mL) at 80 °C and stirred. Subsequently, the reaction mixture was transferred to a pressure tube and the reaction was continued at 120 °C. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed sequentially with water and sodium hydroxide solution (1 equiv., 3 x 5 mL). The organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated and purified by column chromatography to afford the target product, N-methyl dicyclohexylamine.
[1] Tetrahedron Letters, 2017, vol. 58, # 10, p. 909 - 913
