Synthesis of N-ethyldicyclohexylamine

Preparation of N-ethyldicyclohexylamine

Preparation of N-ethyldicyclohexylamine

Preparation of N-ethyldicyclohexylamine

In a 1-litre three-necked flask connected with a reflux condenser, stirrer, and dropping funnel, with the exclusion of moisture, 2 moles of N,N-dicyclohexylamine is heated with 2 moles of diethyl sulfate for 2 hours on a boiling water bath. Stirring is continued for a further 15 hours at this temperature. Then 2.5 moles of 50% potassium hydroxide is stirred into the cooled mixture, the liberated amine is separated off, and the aqueous phase is extracted several times with diethyl ether. The ethereal extracts are combined and dried overnight with sodium hydroxide, the diethyl ether is evaporated off, and the N-ethyldicyclohexylamine is fractionated through a 30-cm Vigreux column in vacuo. B.p. 138°C/14mm, yield 337 g (94%, calculated on the N,N-dicyclohexylamine that has reacted). Unchanged N,N-dicyclohexylamine (about 15%) passes over as fore-run, b.p. 125°C/16mm.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 213, (1973)

IUPAC Name

N-cyclohexyl-N-ethylcyclohexanamine

InChI

InChI=1S/C14H27N/c1-2-15(13-9-5-3-6-10-13)14-11-7-4-8-12-14/h13-14H,2-12H2,1H3

InChI Key

XRKQMIFKHDXFNQ-UHFFFAOYSA-N

Canonical SMILES

CCN(C1CCCCC1)C2CCCCC2

Depositor-Supplied Synonyms

N-Ethyldicyclohexylamine, 7175-49-7, Ethyldicyclohexylamine, N-Cyclohexyl-N-ethylcyclohexanamine, Cyclohexanamine, N-cyclohexyl-N-ethyl-, DICYCLOHEXYLAMINE, N-ETHYL-, dicyclohexylethylamine, N,N-Dicyclohexylethylamine, XRKQMIFKHDXFNQ-UHFFFAOYSA-N, N-Cyclohexyl-N-ethylcyclohexylamine, EINECS 230-534-1, SBB060235, NSC 221147, BRN 2240256, NSC221147, ethyl-dicyclohexylamine, ACMC-20ak4s, AC1L2MMB, SCHEMBL23038, 307017_ALDRICH, MolPort-003-929-733, ZINC1755885, N-Cyclohexyl-N-ethylcyclohexanamine #, AKOS016014071, MCULE-7800803558, NSC-221147, AJ-31486, AK129913, LS-61774, OR013374, OR332399, SC-25288, DB-055565, KB-204108, TC-165763, FT-0636382, ST50405277, I14-93121, 3B3-029073

Removed Synonyms

CID23563, 4-12-00-00024 (Beilstein Handbook Reference)

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