Synthesis of diethylamine (N-ethylethanamine; N,N-diethylamine)

Preparation of diethylamine

50 g of diethylaniline are dissolved in solution of 148 g of hydrochloric acid (d=1.12) in with 75 ml of water. This obtained solution is treated with 32 g of sodium nitrite dissolved in 52 ml of water. During the diazotization reaction the temperature is kept at 0° C. The reaction mixture is allowed to stand for a short time, then run slowly into a boiling solution of 85 g of sodium hydroxide in 2000 ml of water, contained in a vessel provided with a condenser and receiver. The boiling is continued for 45 minutes after all N,N-diethyl-4-nitrosoaniline has been added. Diethylamine is distilled off and is collected in an excess of hydrochloric acid. The solution of diethylamine hydrochloride is then evaporated to dryness and the dry salt gently warmed with 40% sodiumhydroxide solution yielding crude diethylamine which is purified by distillation yielding 75 % of final product with boiling point 55-56° C.

Organic medical chemicals, by M. Barrowliff, 107, 1921

IUPAC Name

N-ethylethanamine

InChI

InChI=1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3

InChI Key

HPNMFZURTQLUMO-UHFFFAOYSA-N

Canonical SMILES

CCNCC

MeSH Synonyms

diethylamine, diethylamine acetate, diethylamine hydrobromide, diethylamine hydrochloride, diethylamine perchlorate, diethylamine phosphate (1:1), diethylamine sulfate, diethylamine sulfite (1:1)

Depositor-Supplied Synonyms

DIETHYLAMINE, N-Ethylethanamine, N,N-Diethylamine, 109-89-7, Ethanamine, N-ethyl-, Diethamine, Diaethylamin, N-Ethyl-Ethanamine, Diethylamin, Dietilamina, Dwuetyloamina, diethyl amine, Diethyl-amine, 2,2′-Diethylamine, Diaethylamin [German], Dietilamina [Italian], Dwuetyloamina [Polish], UNII-B035PIS86W, CCRIS 4792, HSDB 524, (C2H5)2NH, HPNMFZURTQLUMO-UHFFFAOYSA-N, EINECS 203-716-3, UN1154, AI3-24215, di-ethylamine, N,N-diethyl amine, Et2NH, PubChem17237, ACMC-1BS8V, DSSTox_CID_1909, CHEMBL1189, DSSTox_RID_76397, DSSTox_GSID_21909, KSC491S9L, 386456_ALDRICH, 660-68-4 (hydrochloride), AC1L1Q30, AC1Q31K4, B035PIS86W, D0806_SIAL, 6274-12-0 (hydrobromide), 31730_FLUKA, CHEBI:85259, CTK3J1995, 14999-74-7 (perchlorate), 20726-63-0 (acetate), 26292-53-5 (sulfate), MolPort-000-872-068, 31730_SIAL, LTBB000410, 471216_SIAL, Tox21_202506, ANW-16103, CS0041, LS-492, AKOS000269031, MCULE-6895602113, NE10629, RP18324, RTR-002098, UN 1154, NCGC00090709-01, NCGC00090709-02, NCGC00260055-01, 68109-72-8 (phosphate[1:1]), AN-22582, CAS-109-89-7, KB-49828, SC-76785, Diethylamine [UN1154] [Flammable liquid], TR-002098, D0462, Diethylamine [UN1154] [Flammable liquid], FT-0624870, FT-0694952, FT-0694953, 7514-EP2269610A2, 7514-EP2269977A2, 7514-EP2269989A1, 7514-EP2269999A1, 7514-EP2270002A1, 7514-EP2270006A1, 7514-EP2270010A1, 7514-EP2270011A1, 7514-EP2270014A1, 7514-EP2272509A1, 7514-EP2272516A2, 7514-EP2272517A1, 7514-EP2272537A2, 7514-EP2272817A1, 7514-EP2272822A1, 7514-EP2272825A2, 7514-EP2272832A1, 7514-EP2272841A1, 7514-EP2272844A1, 7514-EP2274983A1, 7514-EP2275412A1, 7514-EP2275420A1, 7514-EP2275421A1, 7514-EP2275424A1, 7514-EP2277848A1, 7514-EP2277863A1, 7514-EP2277867A2, 7514-EP2277875A2, 7514-EP2279750A1, 7514-EP2280000A1, 7514-EP2280003A2, 7514-EP2280006A1, 7514-EP2280008A2, 7514-EP2280010A2, 7514-EP2281563A1, 7514-EP2281813A1, 7514-EP2281822A1, 7514-EP2284157A1, 7514-EP2284159A1, 7514-EP2284160A1, 7514-EP2284172A1, 7514-EP2286811A1, 7514-EP2287152A2, 7514-EP2287157A1, 7514-EP2287160A1, 7514-EP2287163A1, 7514-EP2289510A1, 7514-EP2289868A1, 7514-EP2289883A1, 7514-EP2289891A2, 7514-EP2289896A1, 7514-EP2292576A2, 7514-EP2292592A1, 7514-EP2292593A2, 7514-EP2292597A1, 7514-EP2292610A1, 7514-EP2292612A2, 7514-EP2292619A1, 7514-EP2292630A1, 7514-EP2295399A2, 7514-EP2295407A1, 7514-EP2295409A1, 7514-EP2295411A1, 7514-EP2295415A1, 7514-EP2295416A2, 7514-EP2295423A1, 7514-EP2295432A1, 7514-EP2295437A1, 7514-EP2295503A1, 7514-EP2298734A2, 7514-EP2298736A1, 7514-EP2298742A1, 7514-EP2298743A1, 7514-EP2298748A2, 7514-EP2298750A1, 7514-EP2298755A1, 7514-EP2298761A1, 7514-EP2298764A1, 7514-EP2298765A1, 7514-EP2298767A1, 7514-EP2298768A1, 7514-EP2298770A1, 7514-EP2298775A1, 7514-EP2298778A1, 7514-EP2298779A1, 7514-EP2298828A1, 7514-EP2301627A1, 7514-EP2301923A1, 7514-EP2301928A1, 7514-EP2301931A1, 7514-EP2301936A1, 7514-EP2305250A1, 7514-EP2305257A1, 7514-EP2305651A1, 7514-EP2305652A2, 7514-EP2305667A2, 7514-EP2305673A1, 7514-EP2305676A1, 7514-EP2305677A1, 7514-EP2305678A1, 7514-EP2305679A1, 7514-EP2305682A1, 7514-EP2308510A1, 7514-EP2308562A2, 7514-EP2308812A2, 7514-EP2308828A2, 7514-EP2308838A1, 7514-EP2308840A1, 7514-EP2308851A1, 7514-EP2308854A1, 7514-EP2308873A1, 7514-EP2308875A1, 7514-EP2308879A1, 7514-EP2308880A1, 7514-EP2311808A1, 7514-EP2311824A1, 7514-EP2311829A1, 7514-EP2311831A1, 7514-EP2311834A1, 7514-EP2314295A1, 7514-EP2314584A1, 7514-EP2314585A1, 7514-EP2314587A1, 7514-EP2314588A1, 7514-EP2314590A1, 7514-EP2314593A1, 7514-EP2316457A1, 7514-EP2316458A1, 7514-EP2316459A1, 7514-EP2316470A2, 7514-EP2316824A1, 7514-EP2316825A1, 7514-EP2316826A1, 7514-EP2316827A1, 7514-EP2316828A1, 7514-EP2316832A1, 7514-EP2316833A1, 7514-EP2316836A1, 7514-EP2380874A2, 37264-EP2275398A1, 37264-EP2295503A1, 37264-EP2301937A1, 37264-EP2311802A1, 37264-EP2311803A1, 59608-EP2284166A1, 59608-EP2295436A1, 59608-EP2298769A1, 59608-EP2298773A1, 59608-EP2308852A1, 3B4-0273, I14-6018, InChI=1/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H

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