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Levetiracetam
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Name

Levetiracetam

 EINECS 200-659-6
CAS No. 102767-28-2 Density 1.168 g/cm3
PSA 63.40000 LogP 0.51090
Solubility N/A Melting Point 118-119 °C
Formula C8H14N2O2 Boiling Point 395.9 °C at 760 mmHg
Molecular Weight 170.211 Flash Point 193.2 °C
Transport Information N/A Appearance White crystalline powder
Safety 26 Risk Codes 22-36
Molecular Structure Molecular Structure of 102767-28-2 (102767-28-2) Hazard Symbols HarmfulXn
Synonyms

2-(2-oxopyrrolidin-1-yl)butanamide;Keppra (TN);1-Pyrrolidineacetamide,R-ethyl-2-oxo-,(RS)-;Levetiracetamum [INN-Latin];(S)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide;(2R)-2-(2-oxopyrrolidin-1-yl)butanamide;(2S)-2-(2-oxopyrrolidin-1-yl)butanamide;UCB-L 059;Levetiracetam [INN];Keppra;1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-, (S)-;Levetiracetam butanamide;

Article Data 54

Levetiracetam Synthetic route

941289-97-0

1-((S)-1-carbamoylpropyl)-2-oxopyrrolidine-3-carboxylic acid methyl ester

102767-28-2

levetiracetam

Conditions
ConditionsYield
With water; sodium chloride In N,N-dimethyl-formamide at 130 - 140℃; for 18h; Product distribution / selectivity;100%
In 4-methyl-2-pentanone at 115 - 120℃; for 12h; Product distribution / selectivity;52%

dehydro levetiracetam

102767-28-2

levetiracetam

Conditions
ConditionsYield
With C68H72Cl2Co2P4; hydrogen In methanol at 50℃; Reagent/catalyst; enantioselective reaction;99.9%

(2S)-2-(3,4-dichloro-2,5-dihydro-2-oxo-1H-pyrrol-1-yl)butanamide

102767-28-2

levetiracetam

Conditions
ConditionsYield
With hydrogen; triethylamine; palladium on activated charcoal In ethanol under 2587.71 Torr; for 2h;91%
53726-14-0

(S)-2-amino-butanamide hydrochloride

4635-59-0

4-Chlorobutanoyl chloride

102767-28-2

levetiracetam

Conditions
ConditionsYield
Stage #1: (S)-2-amino-butanamide hydrochloride With tetrabutylammomium bromide; sodium sulfate In dichloromethane at 0℃; for 0.5h;
Stage #2: 4-Chlorobutanoyl chloride With potassium hydroxide In dichloromethane at 0℃; for 7h;		89%
Stage #1: (S)-2-amino-butanamide hydrochloride; 4-Chlorobutanoyl chloride With potassium hydroxide; sodium sulfate In acetonitrile at 3 - 5℃; for 5h;
Stage #2: With hydrogenchloride pH=6; Product distribution / selectivity;		84%
With potassium hydroxide; tetrabutylammomium bromide; sodium sulfate; molecular sieve In dichloromethane; ethyl acetate; toluene74.1%
7324-11-0, 53726-14-0, 104652-77-9, 143164-46-9

(S)-2-amino-butanamide

4635-59-0

4-Chlorobutanoyl chloride

102767-28-2

levetiracetam

Conditions
ConditionsYield
Stage #1: (S)-2-amino-butanamide With tetrabutylammomium bromide; potassium hydroxide In dichloromethane at -15 - -5℃; for 2.25h;
Stage #2: 4-Chlorobutanoyl chloride In dichloromethane at -10 - -8℃;		85%
3153-33-1

butyl 4-chlorobutyrate

53726-14-0

(S)-2-amino-butanamide hydrochloride

102767-28-2

levetiracetam

Conditions
ConditionsYield
With triethylamine; sodium iodide In isopropyl alcohol at 90℃; for 36h; Inert atmosphere;85%
102916-46-1

(S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid (R)-α-methylbenzylamine salt

102767-28-2

levetiracetam

Conditions
ConditionsYield
Stage #1: (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid (R)-α-methylbenzylamine salt With sodium hydroxide In water for 0.5h;
Stage #2: With chloroformic acid ethyl ester In dichloromethane at -10℃; for 2h;
Stage #3: With ammonia In dichloromethane at -15 - -10℃; for 2h; Solvent; Reagent/catalyst;		85%
Multi-step reaction with 3 steps
1.1: sodium hydroxide; water / 0.5 h / 0 - 10 °C
1.2: pH 4 - 5
2.1: toluene-4-sulfonic acid / 7 h / 60 °C
3.1: ammonia / 24 h / 0 - 10 °C
View Scheme
3153-36-4

4-chloro-butyric acid ethyl ester

53726-14-0

(S)-2-amino-butanamide hydrochloride

102767-28-2

levetiracetam

Conditions
ConditionsYield
With sodium carbonate; sodium iodide In dimethyl sulfoxide at 90℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;84%
3153-34-2

isopropyl 4-chlorobutanoate

53726-14-0

(S)-2-amino-butanamide hydrochloride

102767-28-2

levetiracetam

Conditions
ConditionsYield
With sodium carbonate; sodium iodide In N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere;83%

(S)-N-[1(aminocarbonyl)propyl]-4-bromobutyramide

102767-28-2

levetiracetam

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;82%

Levetiracetam Specification

1. Introduction of Levetiracetam
Levetiracetam is a white crystalline solid. The IUPAC Name of this chemical is (2R)-2-(2-oxopyrrolidin-1-yl)butanamide. Besides, it belongs to Anticonvulsant;Intermediates & Fine Chemicals;Pharmaceuticals;Miscellaneous Compounds. In addition, the Classification Code of this chemical is Antiepileptic; Drug / Therapeutic Agent. It is very soluble in water and  freely soluble in chloroform (65.3 g/100 mL) and in methanol (53.6 g/100 mL), soluble in ethanol (16.5 g/100 mL), sparingly soluble in acetonitrile (5.7 g/100 mL) and practically insoluble in n-hexane. (Solubility limits are expressed as g/100 mL solvent.)

2. Properties of Levetiracetam
Physical properties about Levetiracetam are:
(1)XLogP3-AA: -0.3; (2)H-Bond Donor: 1; (3)H-Bond Acceptor: 2; (4)Melting Point: 118-119 °C; (5)Surface Tension: 48.8 dyne/cm; (6)Density: 1.168 g/cm3; (7)Flash Point: 193.2 °C; (8)Enthalpy of Vaporization: 64.61 kJ/mol; (9)Boiling Point: 395.9 °C at 760 mmHg; (10)Vapour Pressure: 1.78E-06 mmHg at 25 °C.

3. Structure Descriptors of Levetiracetam
(1)InChI: InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m0/s1
(2)InChIKey: HPHUVLMMVZITSG-LURJTMIESA-N
(3)Canonical SMILES : CCC(C(=O)N)N1CCCC1=O
(4)Isomeric SMILES: CC[C@@H](C(=O)N)N1CCCC1=O
(5)Smiles: N1([C@H](C(=O)N)CC)C(=O)CCC1

4. Toxicity of Levetiracetam

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 1081mg/kg (1081mg/kg)   United States Patent Document. Vol. #4696943,
rat LD50 intravenous 1038mg/kg (1038mg/kg)   United States Patent Document. Vol. #4696943,

5. Safety information of Levetiracetam
Hazard Codes: HarmfulXn
Risk Statements: 22-36 
R22:Harmful if swallowed. 
R36:Irritating to eyes.
Safety Statements: 26 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RTECS: UX9656166

6. Uses of Levetiracetam
Levetiracetam (CAS NO.102767-28-2) is also sometimes used to treat neuropathic pain.It has recently been approved in the United Kingdom as a monotherapy treatment for epilepsy. It is also used in veterinary medicine for similar purposes.

7. Production of Levetiracetam
(1)H-MET-NH2 can be used to manufacture Levetiracetam. The detail is as follows:

Production of Levetiracetam

(2)A reaction flask was added 500ml of methanol and deionized water 33ml, cooled to 0 ° C. Then add with stirring 50.0g (0.27mol), pass ammonia and dissolve to saturation, and seale reaction flask 0 to 5 º C reaction was stirred 96h TLC tracking,eluent, ethyl acetate / acetone (3:1) product Rf = 0.28, raw material Rf = 0.6]. feedstock point disappears, and the end of the reaction. Finanly, it was distilled under reduced pressure to obtain a yellow solid levetiracetam crude product 41.5g and the yield is 90.2%.

Production of Levetiracetam

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