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77472-70-9

Basic Information
CAS No.: 77472-70-9
Name: 1-Pyrrolidineacetamide,2-oxo-4-phenyl-
Molecular Structure:
Molecular Structure of 77472-70-9 (1-Pyrrolidineacetamide,2-oxo-4-phenyl-)
Formula: C12H14N2O2
Molecular Weight: 218.25
Synonyms: 4-Phenyl-2-oxopyrrolidine-1-acetamide;4-Phenylpiracetam;Carphedon;Carphedone;Fonturacetam;Karfedon;Phenotropyl;2-(2-Oxo-4-phenyl-pyrrolidin-1-yl)acetamide;
EINECS: 688-268-0
Density: 1.22 g/cm3
Melting Point: 129.5-130.5 °C(Solv: ethyl acetate (141-78-6))
Boiling Point: 486.4 °C at 760 mmHg
Flash Point: 247.9 °C
Solubility:
Appearance:
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 64.39000
LogP: 1.57540
Synthetic route
70291-40-6

2-oxo-4-phenyl-1-pyrrolidineacetic acid, ethyl ester

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
With ammonia In methanol at 45 - 50℃; for 5h;100%
With ammonium hydroxide for 2h;64%

4-[(2-amino-2-oxoethyl)amino]-3-phenylbutanoic acid

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Heating;97%
68497-63-2

methyl-2-oxo-4-phenylpyrrolidine-1-acetate

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
With ammonium hydroxide for 2h;81%
With ammonia In methanol at 20 - 30℃; for 12h; Concentration; Temperature; Solvent;81%
1198-97-6

4-phenylpyrrolidin-2-one

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) KOH / 1) DMSO, benzene, reflux, 8 h, 2) DMSO, benzene, RT, 1 d
2: 64 percent / 25percent aq. NH3 / 2 h
View Scheme
Multi-step reaction with 3 steps
1: 90 percent / conc. HCl / 0.33 h / Heating
2: 94 percent / Me3SiOTf / 0.5 h / 150 - 155 °C
3: 81 percent / 25percent aq. NH3 / 2 h
View Scheme
Multi-step reaction with 3 steps
1: 90 percent / conc. HCl / 0.33 h / Heating
2: 53 percent / 1 h / 150 - 160 °C
3: 64 percent / 25percent aq. NH3 / 2 h
View Scheme
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) dioxane, 90 deg C, 1 h, 2.) 125 deg C, 5 h
2: 100 percent / NH3 / methanol / 5 h / 45 - 50 °C
View Scheme
106869-48-1

4-phenyl-1-(trimethylsilyl)-2-pyrrolidinone

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / Me3SiOTf / 0.5 h / 150 - 155 °C
2: 81 percent / 25percent aq. NH3 / 2 h
View Scheme
Multi-step reaction with 2 steps
1: 53 percent / 1 h / 150 - 160 °C
2: 64 percent / 25percent aq. NH3 / 2 h
View Scheme
3060-41-1

(±)-3-carboxy-2-phenylpropan-1-aminium chloride

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / 3 h / Heating
2: 94 percent / Me3SiOTf / 0.5 h / 150 - 155 °C
3: 81 percent / 25percent aq. NH3 / 2 h
View Scheme
Multi-step reaction with 3 steps
1: 99 percent / 3 h / Heating
2: 53 percent / 1 h / 150 - 160 °C
3: 64 percent / 25percent aq. NH3 / 2 h
View Scheme
77519-55-2

2-oxo-4-phenylpyrrolidine-3-carboxylic acid

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 58 percent / 0.5 h / 190 °C
2: 1.) NaH / 1.) dioxane, 90 deg C, 1 h, 2.) 125 deg C, 5 h
3: 100 percent / NH3 / methanol / 5 h / 45 - 50 °C
View Scheme
55790-17-5

3-methoxycarbonyl-4-phenyl-2-pyrrolidone

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89.6 percent / 10percent aq. KOH / 5 h / Heating
2: 58 percent / 0.5 h / 190 °C
3: 1.) NaH / 1.) dioxane, 90 deg C, 1 h, 2.) 125 deg C, 5 h
4: 100 percent / NH3 / methanol / 5 h / 45 - 50 °C
View Scheme
103-36-6

ethyl 3-phenyl-2-propenoate

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / methanol; water / 24 h / 20 - 30 °C
2.1: nickel(II) chloride hexahydrate; water; sodium tetrahydroborate / dichloromethane / 5 h / -10 - 30 °C
3.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / -10 °C
3.2: 2 h / -10 - 0 °C
4.1: ammonia / methanol / 12 h / 20 - 30 °C
View Scheme

4-nitro-3-phenylbutanoic acid ethyl ester

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: nickel(II) chloride hexahydrate; water; sodium tetrahydroborate / dichloromethane / 5 h / -10 - 30 °C
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / -10 °C
2.2: 2 h / -10 - 0 °C
3.1: ammonia / methanol / 12 h / 20 - 30 °C
View Scheme

C10H12NO2(1-)*K(1+)

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / 65 - 75 °C
2: acetic acid / ethanol
3: Heating
View Scheme

C12H15N2O3(1-)*K(1+)

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid / ethanol
2: Heating
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
3: acetic acid / ethanol
4: Heating
View Scheme
77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

64-19-7

acetic acid

acetylkarfedon

Conditions
ConditionsYield
With hydrogenchloride for 0.0833333h; Heating;89%
6217-54-5

docosahexaenoic acid

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

1613318-02-7

C34H44N2O3

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: (RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide In N,N-dimethyl-formamide for 2h;
75%
1719-57-9

Chloro(chloromethyl)dimethylsilane

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

N,N-bis-(chloro-dimethyl-silanylmethyl)-2-(2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane In benzene Alkylation; Heating;
77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

2,2,6,6-tetramethyl-4-[(2-oxo-4-phenylpyrrolidin-1-yl)acetyl]-1-oxa-4-aza-2,6-disilacyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hexamethyldisilazane / benzene / Heating
2: sodium hydrogen carbonate / benzene; H2O
View Scheme
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Specification

This chemical is called 4-Phenyl-2-pyrrolidone-1-acetamide, and its IUPAC name is 2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide. With the molecular formula of C12H14N2O2, its molecular weight is 218.25. In addition, the CAS registry number of this chemical is 77472-70-9, and its classification code is Therapeutic Agent.

Other characteristics of the 4-Phenyl-2-pyrrolidone-1-acetamide can be summarised as followings: (1)ACD/LogP: 0.16; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.16; (4)ACD/LogD (pH 7.4): 0.16; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 29.07; (8)ACD/KOC (pH 7.4): 29.07; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 40.62 Å2; (13)Index of Refraction: 1.579; (14)Molar Refractivity: 59.47 cm3; (15)Molar Volume: 178.8 cm3; (16)Polarizability: 23.57×10-24cm3; (17)Surface Tension: 51.4 dyne/cm; (18)Density: 1.22 g/cm3; (19)Flash Point: 247.9 °C; (20)Enthalpy of Vaporization: 75.21 kJ/mol; (21)Boiling Point: 486.4 °C at 760 mmHg; (22)Vapour Pressure: 1.3E-09 mmHg at 25°C.

You can still convert the following datas into molecular structure: 
(1)SMILES: O=C(N)CN2C(=O)CC(c1ccccc1)C2
(2)InChI: InChI=1/C12H14N2O2/c13-11(15)8-14-7-10(6-12(14)16)9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,13,15)
(3)InChIKey: LYONXVJRBWWGQO-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C12H14N2O2/c13-11(15)8-14-7-10(6-12(14)16)9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,13,15)
(5)Std. InChIKey: LYONXVJRBWWGQO-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported 1100mg/kg (1100mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ANALGESIA
Russian Pharmacology and Toxicology Vol. 44, Pg. 22, 1981.
mouse LD50 unreported 1100mg/kg (1100mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: MUSCLE WEAKNESS
Pharmaceutical Chemistry Journal Vol. 14, Pg. 776, 1980.