ChemicalBook > CAS DataBase List > 2',6'-Pipecoloxylidide

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

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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)

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Safety

Hazard Codes: Xi,T
Risk Statements: 25
Safety Statements: 45
RIDADR: UN 2811 6.1 / PGIII
RTECS: TM6076000
HazardClass: 6.1
HS Code: 2933399990

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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..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: M0370020
Product name: Mepivacaine impurity B
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: 40 mg
Price: $225
Updated: 2025/07/31

Sigma-Aldrich

Product number: 1078529
Product name: Bupivacaine Related Compound B
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 50mg
Price: $1470
Updated: 2025/07/31

Sigma-Aldrich

Product number: M0370020
Product name: Mepivacaine impurity B
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: m0370020
Price: $220
Updated: 2024/03/01

TCI Chemical

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

Sigma-Aldrich

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

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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

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View Lastest Price from 2',6'-Pipecoloxylidide manufacturers

Shanghai Joiny Pharmaceutical Co.,LTD

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

Wuhan Biocar Pharmacy CO.,Ltd.

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

Shandong Xuhuang New material CoLTD

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

15883-20-2, 2',6'-PipecoloxylidideRelated Search:

N,N-Dimethylformamide Chlorantraniliprole Benzamide Formamide Bupivacaine-d9 4-Hydroxy-N-desbutyl Bupivacaine 2,6-DIMETHYLANILINE HYDROCHLORIDE Bupivacaine Impurity 1-Butyl-1-oxido-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide hydrochloride Bupivacaine Impurity 2-Piperidone 3,5-Diiodo-L-tyrosine dihydrate 3,3',5,5'-TETRAIODOTHYRO-ACETIC ACID 3,4-Dimethoxy-L-phenylalanine N-(2,6-Diphenylmethyl)-1-piperazine acetylamine N-(2,6-Dimethylphenyl)-2-picolinamide N-(2,4,6-Trichlorophenyl)maleimide Levobupivacaine

Pipecolinoyl-2,6-xylidide

N-(2',6'-dimethylphenyl)-piperidine-2- carboxylic amide

Des-butyl Bupivacaine (Bupivacaine metabolite)

Desbutylbupivacain

N-(2',6'-Dimethylphenyl)-2-Pip

(2RS)-N-(2,6-DIMETHYLPHENYL) -2-PIPERIDINE CARBOXAMIDE

2',6'-Pipecoloxylidide

N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide

2'',6''-PIPECOLINOXYLIDIDE (2-PIPECOLINOXYLIDIDE)

2’,6’-pipecolylxylidine

debutylbupivacaine

demethylmepivacaine

desbutylbupivacaine

n-(2,6-dimethylphenyl)-2-piperidinecarboxamid

n-desbutylbupivacaine

N-(2',6'-dimethylphenl)-2-Piperidine carboxamide

Bupivacaine EP Impurity B

Bupivacaine Impurity 4(EP Impurity B)

Mepivacaine Impurity 2(Mepivacaine EP Impurity B)

Bupivacaine EP Impurity B-d6

N-(2,6-Dimethylphenyl)piperidine-2-carboxamide

N-(2,6-dimethylphenyl)pipecolinamide

6'-DiMethylphenl)-2-piperidine carboxaMide

2-PiperidinecarboxaMide, N-(2,6-diMethylphenyl)-

Bupivacaine Related Compound B (50 mg) ((2RS)-N-(2,6-dimethylphenyl)piperidine-2-carboxamide) (AS)

Bupivacaine IMp. B (EP)

N-DesMethyl Mepivacaine

2-[(2,6-Dimethylphenyl)carbamoyl]piperidine, 2-[(Piperidin-2-ylcarbonyl)amino]-m-xylene

2',6'-Pipecoloxylidide N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide

(RS)-N-(2,6-Dimethylphenyl)piperidine-2-carboxamide

Bupivacaine Related Compound B (50 mg) (N-(2,6-dimethylphenyl)piperidine-2-carboxamide)

N-(2',6'-DINETHYLPHENYL)-2-PIPERIDINECARBOXAMIDE HCL

N-(2',6'- dimethylphenyl)-piperidine-2-

Pipecoloxylidide

<i>N</i>-(2,6-Dimethylphenyl)piperidine-2-carboxamide

Mepivacaine EP Impurity B

(RS)-N-(2,6-Dimethylphenyl)piperidi

N-(2,6-Dimethylphenyl)piperidine-2-carboxamide&gt

PPX

N-(2,6-DimethyL

2', 6'- piperidine peroxide

5 - (2-fluorophenyl) - 1h-pyrrole-3-methylnitrile

Bupivacaine EP Impurity BQ: What is Bupivacaine EP Impurity B Q: What is the CAS Number of Bupivacaine EP Impurity B Q: What is the storage condition of Bupivacaine EP Impurity B Q: What are the applications of Bupivacaine EP Impurity B

PPX-D9

Bupivacaine Related Compound B (N-(2,6-dimethylphenyl)piperidine-2-carboxamide) (1078529)

(2RS)-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

N - (2 ', 6' - xylenyl) - 2-piperidine amide

Bupivacaine USP Related Compound B

2',6'-Pipecoloxylidide (6CI, 7CI, 8CI)

Bupivacaine Hydrochloride Impurity B

Bupivacaine Hydrochloride EP Impurity B

Bupivacaine Impurity 4(Bupivacaine EP Impurity B)

Mepivacaine Hydrochloride Impurity B

N - (2 ', 6' - xylenyl) -2-piperidine formamide

2 6-pipecoloxylidide or 2',6'-Pipecoloxylidide

2 - pipecolinoxylidide IH

N-(2',6'-Dimethylphenyl)-2-piperidinecarboxamide

BUPIVACAINE EP IMP B