Synthesis of betacain (2,2,6-trimethyl-4-piperidinol benzoate)

Preparation of betacain

Preparation of betacain (2,2,6-trimethyl-4-piperidinol benzoate)

Preparation of betacain (2,2,6-trimethyl-4-piperidinol benzoate)

A mixture of equal weights of benzoyl chloride and 2,2,6-trimethyl-4-piperidinol hydrochloride is heated at 130-140° C for 2 hours and then at 160° C until evolution of fumes of hydrogen chloride is no longer noticeable. The reaction is complete in about 3 hours. After cooling the reaction mixture is treated with small quantity of hot water. The cold solution is filtered, and washed with small amounts of cold water until the color has been removed. Crude betacain is dried and washed with ether or benzene to remove side product – benzoic acid. To obtain pure betacain hydrochloride repeated crystallization from water is performed. Betacain hydrochloride forms fine white crystalline powder. The melting point  is 268° C or 278° C (varies depending on literature source). Betacain hydrochloride is soluble in 90 % alcohol.

Organic medical chemicals, by M. Barrowliff, 98-99, 1921

IUPAC Name

(2,2,6-trimethylpiperidin-4-yl) benzoate

InChI

InChI=1S/C15H21NO2/c1-11-9-13(10-15(2,3)16-11)18-14(17)12-7-5-4-6-8-12/h4-8,11,13,16H,9-10H2,1-3H3

InChI Key

ZYHGIAPHLSTGMX-UHFFFAOYSA-N

Canonical SMILES

CC1CC(CC(N1)(C)C)OC(=O)C2=CC=CC=C2

Depositor-Supplied Synonyms

Betacain, Eucaine, Eucaine B, Eucain B, BETA-EUCAINE, Eukain B, .beta.-Eucaine, NSC 49860, 500-34-5, 2,2,6-Trimethyl-4-piperidinol benzoate (ester), 4-Piperidinol, 2,2,6-trimethyl-, benzoate (ester), 2,2,6-trimethylpiperidin-4-yl benzoate, Betacaine, b-Eucaine, AC1Q60WG, Oprea1_276630, Oprea1_675869, SCHEMBL420179, AC1L1V25, CHEBI:35068, CTK4J1989, ZYHGIAPHLSTGMX-UHFFFAOYSA-N, NSC49860, AR-1D0772, NSC-49860, Trimethylbenzoyloxypiperidine (Related), WLN: T6MTJ B1 B1 DOVR& F1, (2,2,6-trimethylpiperidin-4-yl) benzoate, 2,2,6-Trimethyl-4-piperidinyl benzoate #, LS-117210, 4-Piperidinol, 2,2,6-trimethyl-, benzoate, 4-Piperidinol,2,2,6-trimethyl-, 4-benzoate, 4-Piperidinol, 2,2,6-trimethyl-, 4-benzoate, C14167, (2,2,6-TRIMETHYL-4-PIPERIDYL) BENZOATE, 4-Piperidinol,2,6-trimethyl-, benzoate (ester), 4-Piperidinol,2,6-trimethyl-, benzoate (ester), stereoisomer, 4-Piperidinol, 2,2,6-trimethyl-, benzoate (ester), stereoisomer, 4-Piperidinol, 2,2,6-trimethyl-, benzoate (ester), stereoisomer (VAN), 4-Piperidinol, 2,2,6-trimethyl-, benzoate (ester), stereoisomer (VAN) (8CI), 25334-04-7, 46917-18-4, 772990-62-2

Removed Synonyms

UNII-7X49L994AY, C15H21NO2, CID10373, 51929-55-6

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