2',6'-Pipecoloxylidide Chemical Properties

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)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

RTECS 

TM6076000

HazardClass 

6.1

HS Code 

2933399990

2',6'-Pipecoloxylidide Usage And Synthesis

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

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(15883-20-2)Related Product Information

• N,N-Dimethylformamide
• Chlorantraniliprole
• Benzamide
• Formamide
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• 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
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• N-(2,6-Diphenylmethyl)-1-piperazine acetylamine
• N-(2,6-Dimethylphenyl)-2-picolinamide
• N-(2,4,6-Trichlorophenyl)maleimide
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