Synthesis of cyclohexylamine

Preparation of cyclohexylamine (cyclohexanamine; aminocyclohexane; hexahydroaniline; hexahydrobenzenamine)

Cyclohexylamine is obtained, by hydrogenating aniline in hydrochloric-acetic acid in the presence of colloidal platinum.

Preparation of cyclohexylamine (cyclohexanamine; aminocyclohexane; hexahydroaniline; hexahydrobenzenamine)

Preparation of cyclohexylamine (cyclohexanamine; aminocyclohexane; hexahydroaniline; hexahydrobenzenamine)

8.2 ml (8.37 g) of aniline are dissolved in 110 ml glacial acetic acid and added to the colloidal platinum solution containing 1.5 g of platinum. Then 10 ml of 36% hydrochloric acid are added, the hydrogenation vessel is evacuated and connected to the hydrogen reservoir. After 2.5 hours, the calculated amount of hydrogen has been absorbed. Most of the acetic acid is then distilled off in a vacuum, the residue made alkaline with sodium hydroxide solution, and a liquid steam is steam distilled. This distillate is extracted with ether, dried, the ether is removed by evaporation and the residue is distilled. Fraction boiling at 135° C is collected yielding 8 g of cyclohexylamine.

A. Skita and W. Berendt, Ber. Deut. Chem. Ges., 52, 1519 (1919).

IUPAC Name

cyclohexanamine

InChI

InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2

InChI Key

PAFZNILMFXTMIY-UHFFFAOYSA-N

Canonical SMILES

C1CCC(CC1)N

MeSH Synonyms

Cyclohexylamine, Cyclohexylamines

Depositor-Supplied Synonyms

CYCLOHEXYLAMINE, Cyclohexanamine, Aminocyclohexane, 108-91-8, Hexahydroaniline, Hexahydrobenzenamine, Aminohexahydrobenzene, 1-Cyclohexylamine, 1-Aminocyclohexane, Cyclohexyl amine, Aniline, hexahydro-, Cyclohexylamines, Benzenamine, hexahydro-, Aminocylcohexane, cyclohexyl-amine, UNII-I6GH4W7AEG, 1-AMINO-CYCLOHEXANE, Cyclohexylamin, CCRIS 3645, HSDB 918, CHEBI:15773, PAFZNILMFXTMIY-UHFFFAOYSA-N, EINECS 203-629-0, SBB040492, UN2357, BRN 0471175, Cyclohexylamine [UN2357] [Corrosive], AI3-15323, DSSTox_CID_3996, DSSTox_RID_77250, DSSTox_GSID_23996, CAS-108-91-8, cyclohexaneamine, cyclohexylarnine, cyclo-hexylamine, cyclohexane-amine, cyclohexanyl amine, monocyclohexylamine, 4-Cyclohexylamine, ACMC-1BUGG, AC1L1PYL, HAI, I6GH4W7AEG, bmse000451, AC1Q53FD, AC1Q53FE, BIDD:ER0290, C104655_ALDRICH, 240648_ALDRICH, GTPL5507, CHEMBL1794762, BDBM81970, CTK0H8608, MolPort-000-871-531, Tox21_202380, Tox21_300038, ANW-15993, BBL002476, LS-473, STK387114, AKOS000119083, MCULE-7654331405, RP18677, TRA0041577, TRA0099304, UN 2357, Cyclohexylamine [UN2357] [Corrosive], NCGC00247889-01, NCGC00247889-02, NCGC00253922-01, NCGC00259929-01, AJ-61330, AM802905, AN-42915, BC206665, BP-21278, CAS_108-91-8, KB-49244, NCI60_004907, SC-47180, TC-104738, TR-002007, FT-0624217, ST45255365, T7305, X6008, C00571, 46880-EP2272837A1, 46880-EP2277848A1, 46880-EP2277862A2, 46880-EP2281563A1, 46880-EP2284159A1, 46880-EP2284174A1, 46880-EP2287141A1, 46880-EP2292228A1, 46880-EP2292621A1, 46880-EP2295406A1, 46880-EP2295418A1, 46880-EP2298731A1, 46880-EP2298746A1, 46880-EP2298778A1, 46880-EP2305219A1, 46880-EP2305651A1, 46880-EP2308812A2, 46880-EP2308833A2, 46880-EP2308854A1, 46880-EP2311804A2, 46880-EP2311810A1, 46880-EP2380874A2, 56751-EP2284166A1, 56751-EP2298769A1, 56751-EP2308878A2, 4-12-00-00008 (Beilstein Handbook Reference), 3B4-0313, I05-0465, I14-21057, InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H, 143247-75-0, 157973-60-9

Removed Synonyms

ANILINE, Cyclohexylamine.HCl, Cyclohexylamine hydrobromide, CYCLOHEXYLAMMONIUM ION, CID7965, c0494, c0690, cha, D003514, ANL, 62-53-3

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