2',6'-Pipecoloxylidide
- Product Name
- 2',6'-Pipecoloxylidide
- CAS No.
- 15883-20-2
- Chemical Name
- 2',6'-Pipecoloxylidide
- Synonyms
- PPX;PPX-D9;N-(2,6-DimethyL;Pipecoloxylidide;Desbutylbupivacain;debutylbupivacaine;demethylmepivacaine;desbutylbupivacaine;BUPIVACAINE EP IMP B;n-desbutylbupivacaine
- CBNumber
- CB1110009
- Molecular Formula
- C14H20N2O
- Formula Weight
- 232.32
- MOL File
- 15883-20-2.mol
2',6'-Pipecoloxylidide Property
- Melting point:
- 114-1170C
- Boiling point:
- 392.3±42.0 °C(Predicted)
- Density
- 1.087±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 14.85±0.70(Predicted)
- form
- Solid
- color
- White to Almost white
- InChI
- InChI=1S/C14H20N2O/c1-10-6-5-7-11(2)13(10)16-14(17)12-8-3-4-9-15-12/h5-7,12,15H,3-4,8-9H2,1-2H3,(H,16,17)
- InChIKey
- SILRCGDPZGQJOQ-UHFFFAOYSA-N
- SMILES
- N1CCCCC1C(NC1=C(C)C=CC=C1C)=O
- CAS DataBase Reference
- 15883-20-2(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H301Toxic if swalloed
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- M0370020
- Product name
- Mepivacaine impurity B
- Purity
- European Pharmacopoeia (EP) Reference Standard
- Packaging
- 40 mg
- Price
- $225
- Updated
- 2025/07/31
- Product number
- 1078529
- Product name
- Bupivacaine Related Compound B
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 50mg
- Price
- $1470
- Updated
- 2025/07/31
- Product number
- M0370020
- Product name
- Mepivacaine impurity B
- Purity
- European Pharmacopoeia (EP) Reference Standard
- Packaging
- m0370020
- Price
- $220
- Updated
- 2024/03/01
- Product number
- D4348
- Product name
- N-(2,6-Dimethylphenyl)piperidine-2-carboxamide
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 25g
- Price
- $80
- Updated
- 2025/07/31
- Product number
- PHR1756
- Product name
- Bupivacaine Related Compound B
- Purity
- Pharmaceutical Secondary Standard; Certified Reference Material
- Packaging
- 20mg
- Price
- $721.05
- Updated
- 2025/07/31
2',6'-Pipecoloxylidide Chemical Properties,Usage,Production
Chemical Properties
White to Off-White
Uses
A major metabolite of Bupivacaine
Uses
N-(2,6-Dimethylphenyl)-1-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide is a Bupivacaine (B689561) Impurity. Bupivacaine (B689561) is a sodium channel blocker, local anesthetic.
Definition
ChEBI: 2,6-Pipecoloxylidide is an amino acid amide.
Synthesis
39627-98-0
15883-20-2
General procedure for the synthesis of N-(2-dimethylphenyl)-2-piperidinecarboxamide from N-(2-dimethylphenyl)pyridine-2-carboxamide: Example-2 Preparation of pyridine-2-carboxylic acid-2',6'-dimethylphenylamine; To a stainless steel reaction flask equipped with a mechanical stirrer were added 25 g of pyridine-2-carboxylic acid-2',6'-dimethylphenylamine, 625 ml methanol, 63 ml acetic acid and 15 g of Raney nickel. Subsequently, argon was passed into the mixture for 5 minutes to displace the air, the reaction flask was sealed and charged with 18 kg/cm2 (260 psi) of hydrogen. The reaction mixture was heated to 50°C and maintained at the same pressure and temperature for 28-30 hours until the reaction was complete. After completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated in a rotary evaporator. The crude product was dissolved in 250 ml of toluene, transferred to a partition funnel, 250 ml of water was added and alkalized with 50 ml of 20% aqueous sodium hydroxide. The organic layer was separated and the aqueous layer was extracted twice with 100 ml of toluene. The organic layers were combined and dried with anhydrous magnesium sulfate and subsequently concentrated in a rotary evaporator. The resulting crude solid was recrystallized with 70 ml of toluene to give 18.5 g of slightly pink piperidine-2-carboxylic acid-2',6'-dimethylbenzenemethanamine solid in 72% yield with a melting point of 115.7-116.2 °C. 1H NMR (CDCl3, 300 MHz): δ=8.31 (s, 1H), 7.00 (m, 3H), 3.32 (dd, J=3.2 ,9.7Hz, 1H), 3.0 (m, 1H), 2.68 (m, 1H), 2.14 (s, 6H), 1.98 (m, 1H), 1.93 (s, 1H), 1.77 (m, 1H), 1.59-1.50 (m, 2H), 1.47-1.37 (m, 2H) ppm; 13C NMR (CDCl3, 75MHz) : δ=172.1, 134.7, 133.4, 127.6, 126.5, 59.9, 45.3, 30.0, 25.6, 23.6, 18.1 ppm.
References
[1] Patent: WO2009/89842, 2009, A1. Location in patent: Page/Page column 5-6
[2] Patent: US9173877, 2015, B1. Location in patent: Page/Page column 24-25
[3] Patent: JP2016/508956, 2016, A. Location in patent: Paragraph 0093; 0095
[4] Helvetica Chimica Acta, 1959, vol. 42, p. 1324,1326
2',6'-Pipecoloxylidide Preparation Products And Raw materials
Raw materials
Preparation Products
2',6'-Pipecoloxylidide Suppliers
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- sales21@chemicalland21.com
- Country
- South Korea
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View Lastest Price from 2',6'-Pipecoloxylidide manufacturers
- Product
- 2',6'-Pipecoloxylidide 15883-20-2
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 1000kg
- Release date
- 2025-09-22
- Product
- N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide 15883-20-2
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 0.99
- Supply Ability
- 8000kg
- Release date
- 2025-03-10
- Product
- N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide 15883-20-2
- Price
- US $120.00/KG
- Min. Order
- 1KG
- Purity
- 99.99%
- Supply Ability
- 1T
- Release date
- 2025-02-21