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Flupirtine

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Name

Flupirtine

EINECS 260-503-8
CAS No. 56995-20-1 Density 1.35 g/cm3
PSA 89.27000 LogP 3.71060
Solubility 1g/L(temperature not stated) Melting Point 115-116°
Formula C15H17FN4O2 Boiling Point 434.9 °C at 760 mmHg
Molecular Weight 304.324 Flash Point 216.8 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 56995-20-1 (Flupirtine) Hazard Symbols N/A
Synonyms

Carbamicacid, [2-amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-, ethyl ester(9CI);D 9998;Flupirtine;Katadolon;Trancopal Dolo;

Article Data 7

Flupirtine Synthetic route

541-41-3

chloroformic acid ethyl ester

112523-78-1

N6-(4-fluorobenzyl)pyridine-2,3,6-triamine

56995-20-1

Flupirtine

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; Inert atmosphere; Darkness;82%
In 1,4-dioxane at 20℃; for 1h;75%
In tetrahydrofuran Ambient temperature; Yield given;
452-58-4

2,3-Diaminopyridine

56995-20-1

Flupirtine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 41.8 percent / propan-2-ol / 71 h / Heating
2: 52.8 percent / MnO2 / tetrahydrofuran / 18 h / Ambient temperature
3: Na2S2O4 / tetrahydrofuran; H2O / Ambient temperature
4: tetrahydrofuran / Ambient temperature
View Scheme
76902-24-4

spiropyridine>

56995-20-1

Flupirtine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 52.8 percent / MnO2 / tetrahydrofuran / 18 h / Ambient temperature
2: Na2S2O4 / tetrahydrofuran; H2O / Ambient temperature
3: tetrahydrofuran / Ambient temperature
View Scheme
161263-86-1

5'-<(4-fluorobenzyl)amino>spiropyridine>

56995-20-1

Flupirtine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Na2S2O4 / tetrahydrofuran; H2O / Ambient temperature
2: tetrahydrofuran / Ambient temperature
View Scheme
16013-85-7

2,6-dicholoro-3-nitropyridine

56995-20-1

Flupirtine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ammonia / methanol / 20 °C / Inert atmosphere
2: triethylamine / isopropyl alcohol / 3 h / Reflux; Inert atmosphere
3: hydrogenchloride; tin(II) chloride dihdyrate / water / 3 h / 70 °C / Inert atmosphere
4: 1,4-dioxane / 20 °C / Inert atmosphere; Darkness
View Scheme
27048-04-0

2-amino-6-chloro-3-nitropyridine

56995-20-1

Flupirtine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / isopropyl alcohol / 3 h / Reflux; Inert atmosphere
2: hydrogenchloride; tin(II) chloride dihdyrate / water / 3 h / 70 °C / Inert atmosphere
3: 1,4-dioxane / 20 °C / Inert atmosphere; Darkness
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / isopropyl alcohol / 0.5 h / 5 °C
2: palladium on activated charcoal; hydrogen / methanol / 5 h / 20 °C / 1551.49 Torr
3: 1,4-dioxane / 1 h / 20 °C
View Scheme
33400-49-6

2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine

56995-20-1

Flupirtine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; tin(II) chloride dihdyrate / water / 3 h / 70 °C / Inert atmosphere
2: 1,4-dioxane / 20 °C / Inert atmosphere; Darkness
View Scheme
Multi-step reaction with 2 steps
1: palladium on activated charcoal; hydrogen / methanol / 5 h / 20 °C / 1551.49 Torr
2: 1,4-dioxane / 1 h / 20 °C
View Scheme
140-75-0

para-fluorobenzylamine

56995-20-1

Flupirtine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / isopropyl alcohol / 0.5 h / 5 °C
2: palladium on activated charcoal; hydrogen / methanol / 5 h / 20 °C / 1551.49 Torr
3: 1,4-dioxane / 1 h / 20 °C
View Scheme
56995-20-1

Flupirtine

110-16-7

maleic acid

flupirtine maleate

Conditions
ConditionsYield
In Isopropyl acetate; dimethyl sulfoxide at 55℃; for 1h; Temperature; Solvent; Inert atmosphere;96%
56995-20-1

Flupirtine

5-(4-fluorobenzylamino)-1,3-dihydro-2H-imidazo[4,5-b]pyridine-2-one

Conditions
ConditionsYield
at 200℃; for 0.5h;88%

Flupirtine Specification

The Flupirtine with CAS registry number of 56995-20-1 is also known as Flupirtinum. The IUPAC name is Ethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]pyridin-3-yl]carbamate. Its classification codes are Analgesics; Central Nervous System Agents; Peripheral Nervous System Agents; Sensory System Agents. In addition, the formula is C15H17FN4O2 and the molecular weight is 304.32.

Physical properties about Flupirtine are: (1)ACD/LogP: 1.46 ; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.35; (4)ACD/LogD (pH 7.4): 1.45; (5)ACD/BCF (pH 5.5): 5.88; (6)ACD/BCF (pH 7.4): 7.5; (7)ACD/KOC (pH 5.5): 115.33; (8)ACD/KOC (pH 7.4): 147.07; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 48.91Å2; (13)Index of Refraction: 1.661; (14)Molar Refractivity: 83.32 cm3; (15)Molar Volume: 225.2 cm3; (16)Polarizability: 33.03×10-24cm3; (17)Surface Tension: 60.6 dyne/cm; (18)Density: 1.35 g/cm3; (19)Flash Point: 216.8 °C ; (20)Enthalpy of Vaporization: 69.12 kJ/mol ; (21)Boiling Point: 434.9 °C at 760 mmHg ; (22)Vapour Pressure: 9.1E-08 mmHg at 25 °C.

Preparation of Flupirtine: it is prepared by reaction of 2-amino-3-nitro-6-chloro pyridine with p-fluorobenzyl amine. Then restore the resulting product, which is acylated by ethyl chloride. Finally, react with maleate in isopropyl alcohol to obtain the product.

Flupirtine is prepared by reaction of 2-amino-3-nitro-6-chloro pyridine with p-fluorobenzyl amine.

Uses of Flupirtine: it is used as short-term treatment for surgery, trauma, burns and pain caused by toothache. What's more, it can act on the central nervous system without inhibition of respiration or cough.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CCOC(=O)NC1=C(N=C(C=C1)NCC2=CC=C(C=C2)F)N
2. InChI: InChI=1S/C15H17FN4O2/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20)
3. InChIKey: JUUFBMODXQKSTD-UHFFFAOYSA-N

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