| Identification | Back Directory | [Name]
METHYL PIPECOLINATE HYDROCHLORIDE | [CAS]
32559-18-5 | [Synonyms]
H-DL-Pip-OMe·HCl
TIMTEC-BB SBB003755
METHY PIPECOLINATE HCL
METHYL PIPECOLINATE HCL
MethyPipecolinateHydrochloride
METHYL PIPECOLINATE HYDROCHLORIDE
N-methyl pipecolinate hydrochloride
Methyl piperidine-2-carboxylate HCl
pipecolinic acid methyl ester hydrochloride
Methyl 2-piperidinecarboxylate hydrochloride
METHYL PIPERIDINE-2-CARBOXYLATE HYDROCHLORIDE
2-piperidinecarboxylic acid methyl ester hydrochloride
2-Piperidinecarboxylicacid, methyl ester, hydrochloride (1:1) | [EINECS(EC#)]
203-105-6 | [Molecular Formula]
C7H14ClNO2 | [MDL Number]
MFCD00192316 | [MOL File]
32559-18-5.mol | [Molecular Weight]
179.64 |
| Hazard Information | Back Directory | [Uses]
Methyl Pipecolinate Hydrochloride is a reactant for synthesis of a pipecolic linker and antiviral agents. | [General Description]
Methyl pipecolinate hydrochloride is a hydrochloride salt of methyl piperidine-2-carboxylate (methyl pipecolinate). The kinetics of the enzymatic separation of enantiomeric forms of methyl pipecolinate using Candida antarctica Lipase A (CAL-A) has been reported. Its role as catalyst for the standard Diels-Alder reaction has been examined. | [Synthesis]
Synthesis of methylpiperidine-2-carboxylic acid hydrochloride: methanol (1300 mL) was added to a 3000 mL three-necked round bottom flask. The reaction system was cooled to -30°C. Sulfoxide chloride (280 mL) was added slowly and dropwise under stirring conditions while keeping the temperature at -30 °C. Subsequently, piperidine-2-carboxylic acid (100 g, added in batches) was added to the reaction system and the mixture was cooled to 0 °C. The reaction was continuously stirred for 15 h at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC, the unfolding agent was methanol and a few drops of ammonia were added). After completion of the reaction, the reaction mixture was concentrated under vacuum using a rotary evaporator. Toluene (100 mL) was added to the concentrate and kept under reflux conditions. The mixture was again concentrated under vacuum using a rotary evaporator. This toluene addition and concentration step was repeated twice. The final product was 137 g (98% yield) of methylpiperidine-2-carboxylic acid hydrochloride as a white solid. | [References]
[1] European Journal of Organic Chemistry, 2014, vol. 2014, # 29, p. 6467 - 6480
[2] Patent: US2008/200471, 2008, A1. Location in patent: Page/Page column 38; 39
[3] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 5, p. 1199 - 1212
[4] Tetrahedron Letters, 2006, vol. 47, # 29, p. 5017 - 5020
[5] Chemistry - A European Journal, 2010, vol. 16, # 25, p. 7547 - 7553 |
|
|