ChemicalBook--->CAS DataBase List--->32559-18-5

32559-18-5

32559-18-5 Structure

32559-18-5 Structure
IdentificationBack 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
Chemical PropertiesBack Directory
[Melting point ]

205 °C (dec.)(lit.)
[storage temp. ]

Sealed in dry,Room Temperature
[Appearance]

White to off-white Solid
[InChI]

1S/C7H13NO2.ClH/c1-10-7(9)6-4-2-3-5-8-6;/h6,8H,2-5H2,1H3;1H
[InChIKey]

APCHKWZTSCBBJX-UHFFFAOYSA-N
[SMILES]

Cl.COC(=O)C1CCCCN1
Safety DataBack Directory
[Symbol(GHS) ]

GHS hazard pictograms
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-37/39
[WGK Germany ]

3
[HazardClass ]

IRRITANT
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazard InformationBack 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]

Methanol

67-56-1

DL-Pipecolinic acid

4043-87-2

METHYL PIPECOLINATE HYDROCHLORIDE

32559-18-5

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
Spectrum DetailBack Directory
[Spectrum Detail]

METHYL PIPECOLINATE HYDROCHLORIDE(32559-18-5)1HNMR
METHYL PIPECOLINATE HYDROCHLORIDE(32559-18-5)FT-IR
METHYL PIPECOLINATE HYDROCHLORIDE(32559-18-5)IR
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