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| CAS No.: | 102767-28-2 |
|---|---|
| Name: | 102767-28-2 |
| Article Data: | 54 |
| Molecular Structure: | |
|
|
|
| Formula: | C8H14N2O2 |
| Molecular Weight: | 170.211 |
| 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; |
| EINECS: | 200-659-6 |
| Density: | 1.168 g/cm3 |
| Melting Point: | 118-119 °C |
| Boiling Point: | 395.9 °C at 760 mmHg |
| Flash Point: | 193.2 °C |
| Appearance: | White crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-36 |
| Safety: | 26 |
| PSA: | 63.40000 |
| LogP: | 0.51090 |
- 144851-82-1METHYL2-AMINO-3-FLUOROBENZOATE
- 483366-12-7(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine
- 173606-50-3BOC-10-AMINODECANOIC ACID
- 361456-36-2METHYL (R)-(+)-ISOCYANATO-3-PHENYLPROPI&
- 5156-58-1N-(1-Benzyl-4-pipperidinyl)-N-phenylpropanamide HCl
- 81281-59-67-Benzylideneaminotheophylline
- 50288-62-5threo-Phenyl-2-piperidyl acetamide
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 47087-37-6Z-D-Glu-OMe
- 1219080-61-1IMIDAZOLE-2-BORONIC ACID
- 941289-97-0
1-((S)-1-carbamoylpropyl)-2-oxopyrrolidine-3-carboxylic acid methyl ester
- 102767-28-2
levetiracetam
| Conditions | Yield |
|---|---|
| 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% |
- 102767-28-2
levetiracetam
| Conditions | Yield |
|---|---|
| With C68H72Cl2Co2P4; hydrogen In methanol at 50℃; Reagent/catalyst; enantioselective reaction; | 99.9% |
- 102767-28-2
levetiracetam
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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; toluene | 74.1% |
- 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With sodium carbonate; sodium iodide In N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere; | 83% |
- 102767-28-2
levetiracetam
| Conditions | Yield |
|---|---|
| With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 82% |
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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: 
Xn
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:
(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%.
