Fujita, Tadashi published the artcileCarnitine. I. Hydrolysis of carnitine nitrile chloride with concentrated hydrochloric acid, Related Products of chlorides-buliding-blocks, the publication is Chemical & Pharmaceutical Bulletin (1961), 661-5, database is CAplus.
The hydrolysis of [Me3NCH2CH(OH)CH2CN]Cl (I) was studied as a possible preparation of carnitine (II), and as a check on the preparation of [Me3CH2CH(CH2CO2H)O2CCH2CH(OH)CH2NMe3]2Cl (III) (Dechamps, et al., CA 49, 3816b). I (45 g.) stirred 10 hrs. in an autoclave at 120-30° with 75 cc. concentrated HCl, and the mixture kept overnight at room temperature yielded 83.8% NH4Cl, from the evaporated filtrate 31 g. crystalline compound (IV), m. 180-90° (decomposition), and from the mother liquor from IV 0.8 g. (Me3NCH2CH:CHCO2H)Cl (V), m. 202-3° (decomposition). Comparison of the infrared spectra of IV, V, and [Me3NCH2CH(OH)CH2CO2H]Cl (VI) (curves shown) indicated that IV was a mixture of V and VI. To confirm this, 3.6 g. IV was catalytically reduced (PtO2) in EtOH and yielded 0.2 g. VI, m. 195-6% and 0.6 g. mixture, m. 147-90°, probably VI mixed with (Me3NCH2CH2-CH2CO2H)Cl. IV (25 g.) was also separated by fractional crystallization with 95% EtOH into 4.6 g. V and 1.5 g. VI. VI (19.8 g.) hydrolyzed as was I yielded 7.6 g.V. Modifying the hydrolysis of I by stirring only 4 hrs. on a boiling water bath suppressed the formation of V and yielded 85% pure VI. Thus, III could not be detected as a hydrolysis product of I. Salts of II were reported: sulfamate, m. 1478°; eyclohexanesulfamate, m. 121-2°; sulfate, m. 156-7°; nitrate, m. 79-81°; orotate, m. 191°.
Chemical & Pharmaceutical Bulletin published new progress about 6249-56-5. 6249-56-5 belongs to chlorides-buliding-blocks, auxiliary class Phase Transfer Catalyst,Inhibitor,Natural product, name is 3-Carboxy-N,N,N-trimethylpropan-1-aminium chloride, and the molecular formula is C7H16ClNO2, Related Products of chlorides-buliding-blocks.
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