R-3-AMINOPIPERIDINE DIHCL
(R)-3-aminopiperidine dihydrochloride
CAS: 334618-23-4
Molecular Formula: C5H14Cl2N2
R-3-AMINOPIPERIDINE DIHCL - Names and Identifiers
R-3-AMINOPIPERIDINE DIHCL - Physico-chemical Properties
| Molecular Formula | C5H14Cl2N2 |
| Molar Mass | 173.08406 |
| Melting Point | 190-195°C |
| Solubility | Methanol (Slightly), Water (Slightly) |
| Appearance | Crystallization |
| Color | White to tan |
| Storage Condition | Inert atmosphere,Room Temperature |
| Sensitive | Hygroscopic |
| MDL | MFCD06799458 |
R-3-AMINOPIPERIDINE DIHCL - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| WGK Germany | 2 |
| FLUKA BRAND F CODES | 10-21 |
| HS Code | 29339900 |
R-3-AMINOPIPERIDINE DIHCL - Reference Information
| Use | (R)-3-aminopiperidine dihydrochloride has been used to prepare dipeptidyl peptidase derived from alogliptin Reactants of IV inhibitors. The reagent is used as a heterocyclic diamine N-arylation reactant; the synthesis of reactants of substituted quinolones can reduce the risk of phototoxicity. |
| Overview | ( R)-3-aminopiperidine dihydrochloride, as a primary compound, is an important intermediate in chemical and pharmaceutical drug synthesis, and has important applications in the chemical and pharmaceutical industries. It is an important intermediate for new fine chemicals, low-toxic pesticides, high value-added medicines and chemical additives, the pharmaceutical industry is mainly used to synthesize dipeptidyl peptidase IV( DPP-IV) inhibitors, such as tragliptin, alogliptin and other diabetes drugs. The market demand is large and has certain research significance. |
| synthesis process | (R)-3-aminopiperidine dihydrochloride mainly has the following synthesis methods: 1. using 3-aminopyridine as the starting material, racemic 3-aminopiperidine is obtained through catalytic hydrogenation reduction, and then separated with chiral reagent, (R)-3-aminopiperidine is obtained. This method has a low yield, and an autoclave and an expensive catalyst are required for the catalytic reduction of 3-aminopyridine, which is difficult in actual operation; 2, Using D-ornithine hydrochloride as the starting material, it reacts with dichlorosulfoxide between -78-45 ℃, then the crude (R)-3-aminopiperidine-2-one is obtained through a strong basic anion exchange resin. After purification, it is reduced to (R)-3-aminopiperidine-2-one by LiAlH4, and finally to hydrochloride. This method uses chiral raw material ornithine as the starting material. The racemic phenomenon will occur during the synthesis process. At the same time, ornithine is expensive, and the reaction is carried out at a deep low temperature (-78 ℃), the operability is poor, and lithium tetrahydroaluminum, which is easy to explode, is used at the same time, which increases the operating cost; 3, nicotinamide is used as raw material through catalytic hydrogenation reduction, Boc protection, Hofman degradation, chiral resolution, and deprotection into hydrochloride. The reaction conditions in this step are milder than the previous routes. Although the conditions are more stringent during the catalytic hydrogenation of nicotinamide, there is a lot of room for improvement; 4. using racemic 3-piperidine formamide as raw material, (S)-3-piperidine formamide is decomposed by bacteria (Cupriavidussp. KNK-J915) to obtain (R)-3-piperidine formamide, then boc protection of amino group, Hofman degradation, deprotection to hydrochloride, this method is relatively novel, the isomer of S configuration is decomposed by bacteria (Cupriavidus sp. KNK-J915) as a carbon source to obtain the R-type isomer of opposite configuration. However, the separation process of bacterial decomposition is very demanding and the operation cost is high, so it is difficult to realize industrial large-scale production for the time being. |
Last Update：2024-04-09 15:16:50
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