| Identification | More | [Name]
(R)-3-Piperidinamine dihydrochloride | [CAS]
334618-23-4 | [Synonyms]
(R)-(-)-3-AMINOPIPERIDINE 2HCL
(R)-3-AMINOPIPERIDINE 2HCL
R-3-AMINOPIPERIDINE DIHCL
(R)-(-)-3-AMINOPIPERIDINE DIHYDROCHLORIDE
(R)-3-AMINOPIPERIDINE DIHYDROCHLORIDE
(R)-3-PIPERIDINAMINE DIHYDROCHLORIDE
(R)-PIPERIDIN-3-YLAMINE DIHYDROCHLORIDE
(R)-PIPERIDINE-3-AMINE DIHYDROCHLORIDE
(R)-PIPERIDIN-3-AMINE DIHYDROCHLORIDE
(R)-piperidin-3-amine | [EINECS(EC#)]
608-870-9 | [Molecular Formula]
C5H14Cl2N2 | [MDL Number]
MFCD06799458 | [Molecular Weight]
173.08 | [MOL File]
334618-23-4.mol |
| Questions And Answer | Back Directory | [Preparation]
The main synthetic methods for (R)-3-Piperidinamine dihydrochloride are as follows: 1. Starting with 3-aminopyridine, racemic 3-aminopiperidine is obtained by catalytic hydrogenation reduction, followed by resolution with a chiral reagent to obtain (R)-3-aminopiperidine. This method has a low yield and requires a high-pressure reactor and expensive catalysts for the catalytic reduction of 3-aminopyridine, making it difficult to operate in practice. 2. Starting with D-ornithine hydrochloride, it is reacted with thionyl chloride between -78 and 45 °C, and then passed through a strongly basic anion exchange resin to obtain crude (R)-3-aminopiperidine-2-one. After purification, it is reduced to (R)-3-aminopiperidine by LiAlH4, and finally to hydrochloride. This method uses chiral ornithine as the starting material, and racemic reaction occurs during the synthesis process. Ornithine is expensive, and the reaction is carried out at a very low temperature (-78 °C), making it difficult to operate. In addition, it uses lithium aluminum hydride, which is prone to explosion, increasing the operating cost. 3. Using nicotinamide as a raw material, catalytic hydrogenation reduction, Boc protection, Hofman degradation, chiral resolution, and deprotection to form hydrochloride are employed. This step involves milder reaction conditions compared to the previous routes. Although the catalytic hydrogenation of nicotinamide is relatively demanding, there is significant room for improvement. 4. Using racemic 3-piperidincarboxamide as a raw material, (S)-3-piperidincarboxamide is decomposed by bacteria (Cupriavidus sp. KNK-J915) to obtain (R)-3-piperidincarboxamide. Then, the amino group undergoes Boc protection, Hofman degradation, and deprotection to form hydrochloride. This method is relatively novel, using bacteria (Cupriavidus sp. KNK-J915) to decompose the S-configuration isomer as a carbon source to obtain the opposite R-configuration isomer. However, the bacterial decomposition separation process requires high precision and has high operating costs, making large-scale industrial production currently difficult. |
| Chemical Properties | Back Directory | [Melting point ]
190-195 °C
| [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Methanol (Slightly), Water (Slightly) | [form ]
Powder | [color ]
White to tan | [Optical Rotation]
[α]/D -2.0±0.5°, c = 1 in H2O | [Sensitive ]
Hygroscopic | [InChI]
InChI=1/C5H12N2.ClH/c6-5-2-1-3-7-4-5;/h5,7H,1-4,6H2;1H/t5-;/s3 | [InChIKey]
GGPNYXIOFZLNKW-ZJIMSODOSA-N | [SMILES]
N[C@H]1CNCCC1.Cl |&1:1,r| | [CAS DataBase Reference]
334618-23-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H302-H315-H318-H335 | [Precautionary statements ]
P261-P280-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [WGK Germany ]
2
| [F ]
10-21 | [REACH Registrations]
Active | [HS Code ]
29333220 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
(R)-3-Aminopiperidine Dihydrochloride has been used as a reactant for the preparation of dipeptidyl peptidase IV inhibitors derived from Alogliptin. |
|
| Company Name: |
Ereal Chemical Co., Ltd. Gold
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0831-6888461 15181138905 |
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J & K SCIENTIFIC LTD.
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18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
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Alfa Aesar
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400-6106006 |
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http://chemicals.thermofisher.cn |
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Energy Chemical
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400-0056266 |
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www.energy-chemical.com |
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