Synthesis of benzylamine

Preparation of benzylamine

Benzylamine is prepared by reacting benzyl chloride with hexamethylenetetramine. If ammonia itself is used, the mixture of primary, secondary, and tertiary amines is formed, and the yield of benzylamine is poor.

Preparation of benzylamine

Preparation of benzylamine

To the round bottom flask fitted with reflux condenser and stirrer 70 g of benzyl chloride are added to a suspension of 70 g of finely powdered hexamethylenetetramine in 4 parts of chloroform. The flask is heated under reflux and removed if necessary until the initially often vigorous reaction is over. To complete the reaction the mixture is heated one-half hour longer. Then the flask is cooled, the residue is filtered, washed with small amount of chloroform and dried. The dried residue is transferred to a distilling flask fitted with a condenser and treated with the of 95 per cent alcohol and small excess of concentrated hydrochloric acid. The flask is gently warmed until crystals of ammonium chloride begin to separate. If necessary the heat source should be removed to prevent that the reaction does not become violent. The flask is cooled to room temperature, ammonium chloride and benzylamine hydrochloride crystals are filtered. For addition amount of benzylamine hydrochloride the filtrate is returned to the flask, and treated again with small excess of hydrochloric acid-alcohol mixture. All the procedures are repeated as described above. The combined residues of benzylamine hydrochloride are collected in the flask and dissolved in distilled water, chilled, and the solution made alkaline by adding concentrated solution of sodium hydroxide. The benzyl amine layer is separated, dried over sodium hydroxide, and distilled yielding 45 g of benzyl amine with boiling point 184° C.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 24-27, 1923





InChI Key


Canonical SMILES


MeSH Synonyms

benzylamine, benzylamine hydrobromide, benzylamine hydrochloride, benzylamine monosulfate

Depositor-Supplied Synonyms

BENZYLAMINE, Benzenemethanamine, phenylmethanamine, 100-46-9, Monobenzylamine, alpha-Aminotoluene, (Phenylmethyl)amine, 1-phenylmethanamine, (Aminomethyl)benzene, N-Benzylamine, Phenylmethylamine, Moringine, Sumine 2005, benzyl amine, benzyl-amine, omega-Aminotoluene, .alpha.-Aminotoluene, .omega.-Aminotoluene, CHEBI:40538, Sumine 2006, NSC 8046, HSDB 2795, WGQKYBSKWIADBV-UHFFFAOYSA-N, EINECS 202-854-1, SBB040473, BRN 0741984, AI3-15299, ABN, benzylarnine, Aminotoluene, Apo-Benzydamine, aminomethylbenzene, 1utj, 1utn, 2bza, Phenyl-Methanamine, Benzylamine derivative, N-(phenylmethyl)amine, QuadraPure® BZA, QuadraPure(TM) BZA, AC1L1OWS, DSSTox_CID_1839, SCHEMBL373, TOLUENE,ALPHA-AMINO, ACMC-20aj53, CHEMBL522, Epitope ID:141489, QuadraPure(TM) Benzylamine, QuadraPure® Benzylamine, DSSTox_RID_76359, NCIOpen2_007746, UNII-A1O31ROR09, DSSTox_GSID_21839, KSC178S3P, 185701_ALDRICH, 407712_ALDRICH, 442483_SUPELCO, 668591_ALDRICH, A1O31ROR09, AC1Q540V, 13180_FLUKA, CTK0H8937, NSC8046, CHEBI:109913, MolPort-000-871-513, CID12555, NSC-8046, STR00195, Tox21_300933, DCL000717, DCL000718, STL115534, AKOS000119096, DB02464, EBD2211112, MCULE-6894874255, RP18881, RTR-000182, 3287-99-8 (HYDROCHLORIDE), NCGC00166029-01, NCGC00166029-02, NCGC00254835-01, AJ-55806, AK113063, AN-24552, CAS-100-46-9, KB-47866, LS-43150, ST2413668, TL8000053, TR-000182, B0406, FT-0622834, ST45255426, AZ0001-0093, C15562, 13743-EP2269992A1, 13743-EP2270010A1, 13743-EP2272517A1, 13743-EP2277848A1, 13743-EP2277881A1, 13743-EP2280001A1, 13743-EP2280008A2, 13743-EP2281563A1, 13743-EP2281818A1, 13743-EP2284171A1, 13743-EP2284172A1, 13743-EP2284174A1, 13743-EP2287141A1, 13743-EP2287163A1, 13743-EP2289891A2, 13743-EP2289892A1, 13743-EP2292593A2, 13743-EP2295406A1, 13743-EP2295414A1, 13743-EP2295420A1, 13743-EP2295429A1, 13743-EP2295432A1, 13743-EP2295437A1, 13743-EP2298729A1, 13743-EP2298775A1, 13743-EP2298779A1, 13743-EP2305250A1, 13743-EP2305651A1, 13743-EP2305654A1, 13743-EP2305666A1, 13743-EP2305678A1, 13743-EP2305687A1, 13743-EP2305695A2, 13743-EP2305696A2, 13743-EP2305697A2, 13743-EP2305698A2, 13743-EP2308510A1, 13743-EP2308562A2, 13743-EP2308812A2, 13743-EP2308838A1, 13743-EP2308841A2, 13743-EP2308851A1, 13743-EP2308854A1, 13743-EP2308867A2, 13743-EP2308870A2, 13743-EP2311804A2, 13743-EP2311815A1, 13743-EP2311837A1, 13743-EP2314593A1, 13743-EP2316836A1, 13743-EP2371810A1, 13743-EP2371811A2, 13743-EP2380871A1, 13925-EP2295437A1, 13925-EP2298775A1, 13925-EP2298776A1, 13925-EP2308833A2, 13925-EP2311837A1, 13925-EP2314586A1, 13925-EP2316836A1, 4-12-00-02155 (Beilstein Handbook Reference), I01-2045, BRD-K76133116-001-01-2, 3B3-034762, 3F830B2A-ABAA-4E26-971C-53B1C7485954, InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H, 857483-23-9, 858831-93-3

Removed Synonyms

Bencidamina, Benzidamina, Benzidamine, Benzindamine, Benzydaminum, Benzylamines, |A-Aminotoluene, alpha Aminotoluene, Benzydamine (INN), BENZYDAMINE, Benzidamina [DCIT], benzylamine monosulfate, benzylamine hydrobromide, Apo-Benzydamine (TN), Benzylamine hydrochloride, AC1L1ZUF, AC1Q4XUF, Benzydamine [INN:BAN], Prestwick0_000297, Prestwick1_000297, Prestwick2_000297, Prestwick3_000297, Benzydaminum [INN-Latin], Bencidamina [INN-Spanish], Benzydamine Monohydrochoride, AC1Q3WS9, BSPBio_000234, CHEMBL12610, SPBio_002453, BPBio1_000258, STOCK6S-01108, C19H23N3O, CID7504, MolPort-001-684-202, HMS2090P22, 132-69-4 (mono-hydrochloride), EINECS 211-388-8, STK711092, BRN 0896536, NCGC00016397-01, NCGC00016397-02, AC-15604, CAS-132-69-4, LS-81420, TL8004545, C 1523, D07516, 5-23-11-00248 (Beilstein Handbook Reference), C030796, D001596, 1-Benzyl-3-(3-(dimethylamino)propoxy)-1H-indazole, 1H-Indazole, 1-benzyl-3-(3-(dimethylamino)propoxy)-, BRD-K28542495-003-03-6, {3-[(1-benzyl-1H-indazol-3-yl)oxy]propyl}dimethylamine, 3-(1-benzylindazol-3-yl)oxy-N,N-dimethylpropan-1-amine, 3-[(1-benzyl-1H-indazol-3-yl)oxy]-N,N-dimethylpropan-1-amine, 1-Propanamine, N,N-dimethyl-3-((1-(phenylmethyl)-1H-indazol-3-yl)oxy)-, 1-Propanamine, N,N-dimethyl-3-[[1-(phenylmethyl)-1H-indazol-3-yl]oxy]-, 642-72-8

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