Synthesis of amylocaine (1-((dimethylamino)methyl)-1-methylpropyl benzoate)

Preparation of amylocaine

Preparation of amylocaine (1-((dimethylamino)methyl)-1-methylpropyl benzoate)

Preparation of amylocaine (1-((dimethylamino)methyl)-1-methylpropyl benzoate)

100 g of 1-(dimethylamino)-2-methylbutan-2-ol are mixed with a solution of 115 g of benzoyl chloride dissolved in 200 g of benzol. The reaction starts by the evaluation of heat and the hydrochloride of amylocaine separates. The reaction is complete by boiling for some time and then the reaction mixture is cooled, the crystals are filtered off, washed with cold benzol and recrystallized from absolute alcohol, or by dissolving in the minimum amount of methyl alcohol and mixing with an equal volume of acetone. Amylocaine  forms small colorless, glistening, scaly crystals, which melt at 175° C. Amylocaine is very soluble in water, readily soluble in alcohol and almost insoluble in ether.

Organic medical chemicals, by M. Barrowliff, 101-102, 1921

IUPAC Name

[1-(dimethylamino)-2-methylbutan-2-yl] benzoate

InChI

InChI=1S/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3

InChI Key

FDMBBCOBEAVDAO-UHFFFAOYSA-N

Canonical SMILES

CCC(C)(CN(C)C)OC(=O)C1=CC=CC=C1

MeSH Synonyms

Amyleine, amylocaine, amylocaine hydrochloride, Dolodent, Stovaine

Depositor-Supplied Synonyms

Amylocaine, Amyleine, Stovaine, 644-26-8, CHEBI:34981, Amylocaine (BAN), Amylocaine [BAN], EINECS 211-411-1, BRN 2453568, 1-((Dimethylamino)methyl)-1-methylpropyl benzoate, 2-Butanol, 1-(dimethylamino)-2-methyl-, benzoate, 1-(DIMETHYLAMINO)-2-METHYL-2-BUTANOL BENZOATE, 2-Butanol, 1-(dimethylamino)-2-methyl-, benzoate (ester), 1-[(Dimethylamino)methyl]-1-methylpropyl benzoate, Stovine, AC1L1VWH, Prestwick0_000049, Prestwick1_000049, Prestwick2_000049, Prestwick3_000049, SCHEMBL81360, BSPBio_000177, SPBio_002098, 532-59-2 (hydrochloride), BPBio1_000195, CHEMBL1740065, CTK8J8334, FDMBBCOBEAVDAO-UHFFFAOYSA-N, 1-[ methyl]-1-methylpropylbenzoate, NCGC00179641-01, LS-46515, 1-(Dimethylaminomethyl)-1-methylpropyl benzoate, C14169, D07454, [1-(dimethylamino)-2-methylbutan-2-yl] benzoate, 4-09-00-00566 (Beilstein Handbook Reference), 1-[(Dimethylamino)methyl]-1-methylpropyl benzoate #, BRD-A09062839-003-03-5

Removed Synonyms

UNII-QRW683O56T, C14H21NO2, CID10767

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