Gabapentin-lactam supplier | CasNO.64744-50-9

Name
Gabapentin-lactam
EINECS 451-630-1
CAS No. 64744-50-9
Article Data24
CAS DataBase
Density 1.05 g/cm³
Solubility
Melting Point 84-89 °C(lit.)
Formula C₉H₁₅NO
Boiling Point 330.1 °C at 760 mmHg
Molecular Weight 153.224
Flash Point 192.3 °C
Transport Information
Appearance white solid
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3,3-Pentamethylene-4-butyrolactam;2-Azaspiro[4.5]decan-3-one;
PSA 29.10000
LogP 1.78560

Synthetic route

: 99189-60-3
[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 40℃; for 3.5h; Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=8.2 - 8.8; Product distribution / selectivity; Heating / reflux;	100%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 50℃; for 3h; Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=11 - 12; Product distribution / selectivity;	93.8%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide In water at 20 - 30℃; for 0.5h; Stage #2: With sode de l'acide trichloroisocyanurique In water at 0 - 20℃; for 5h; Stage #3: In water; toluene at 80℃; for 8h; Reagent/catalyst;	85%
Multi-step reaction with 2 steps 1.1: trichloroisocyanuric acid / methanol / 1.75 h / 20 - 25 °C 2.1: sodium hydroxide / water / 4 h / 0 - 20 °C 2.2: 8 h / 80 °C View Scheme

: 133481-09-1
(1-cyanocyclohexyl)-acetic acid

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Stage #1: (1-cyanocyclohexyl)-acetic acid With sodium hydroxide In water pH=12; Stage #2: With hydrogen In water; toluene at 80 - 85℃; under 3750.38 - 7500.75 Torr; Inert atmosphere;	97.3%
With chromium-promoted Raney-nickel; hydrogen In water at 110℃; under 15757.7 Torr; for 9h; Reagent/catalyst; Temperature; Autoclave;	95.3%

: 4172-99-0
(1-cyanocyclohexyl)acetonitrile

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Stage #1: (1-cyanocyclohexyl)acetonitrile With sodium hydrogencarbonate at 25℃; for 28h; pH=7.4 - 7.5; Enzymatic reaction; Stage #2: With sodium hydroxide In water at 20℃; Stage #3: With hydrogen In water at 80℃; under 7500.75 Torr; Concentration; Time; Inert atmosphere;	93.63%

: 1130-32-1
3-azaspiro[5,5]undecane-2,4-dione

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
With methanol; tert-butylhypochlorite; potassium tert-butylate; potassium bromide at 60℃; for 24h; Hofmann type rearrangement; Inert atmosphere;	92%
With bromine; sodium hydroxide In water at 0 - 85℃; Product distribution / selectivity;

: 955362-91-1
1-(aminomethyl)cyclohexaneacetic acid potassium salt

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
With 4-methyl-morpholine; bis(trichloromethyl) carbonate; potassium hydroxide In water; acetonitrile at 20℃; for 0.00277778h; Inert atmosphere;	92%

: (1-cyanocyclohexyl)acetic acid sodium salt

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
With Raney Nickel In water at 80℃; under 7500.75 Torr; for 18h; pH=13.5;	91.9%

: 133938-45-1
ethyl 1-nitromethyl-1-cyclohexaneacetate

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
In palladium-carbon; ethanol	91.6%

: (+/-)-(5R,6S)-2-(benzoylamino)-4,4,6-trichloro-3-oxo-2-azaspiro[4.5]decane

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
With nickel In ethanol at 110℃; for 21h;	90%

: (1-cyanocyclohexyl)acetic acid barium salt

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
With hydrogen In water at 80℃; under 7500.75 Torr; for 20h; pH=13.5;	90%

: C10H16ClNO3

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Stage #1: C10H16ClNO3 With sodium hydroxide In water at 0 - 20℃; for 4h; Stage #2: In toluene at 80℃; for 8h;	90%

: 608532-82-7
2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃;	83%

cyclohexane-diacetic acid-(1.1)-anhydride: cyclohexane-diacetic acid-(1.1)-anhydride

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
With ammonia Zersetzen des Ammoniumsalzes mit 1.1 Mol 10%iger Natronlauge, Behandeln des Reaktionsprodukts mit alkal.Kaliumhypobromit-Loesung, zuletzt bei 70-75grad, und Eindampfen mit Salzsaeure;

: 2-(dimethylamino)-2-azaspiro[4.5]decan-3-one

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
With magnesium monoperoxyphthalate hexahydrate In methanol at 20℃; for 3h;	39 mg

: 1192-88-7
1-cyclohexene-1-carboxaldehyde

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: CH2Cl2 / 20 °C 2.1: DMAB; methanesulfonic acid / diethyl ether / 3 h / 0 °C 2.2: 81 percent / pyridine / CH2Cl2 / 0 °C 3.1: 77 percent / CuCl; TMEDA / acetonitrile / 20 h / 60 °C 4.1: 90 percent / Raney-Ni / ethanol / 21 h / 110 °C View Scheme

: 1-cyclohexen-1-carboxaldehyde benzoylhydrazone

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: DMAB; methanesulfonic acid / diethyl ether / 3 h / 0 °C 1.2: 81 percent / pyridine / CH2Cl2 / 0 °C 2.1: 77 percent / CuCl; TMEDA / acetonitrile / 20 h / 60 °C 3.1: 90 percent / Raney-Ni / ethanol / 21 h / 110 °C View Scheme

: 651311-40-9
N'-(1-cyclohexenylmethyl)-N'-trichloroacetylbenzohydrazide

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / CuCl; TMEDA / acetonitrile / 20 h / 60 °C 2: 90 percent / Raney-Ni / ethanol / 21 h / 110 °C View Scheme

: 219915-83-0
[1-Cyclohexyl-meth-(E)-ylidene]-(4-methoxy-benzyl)-amine

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene / 1 h / 0 - 20 °C 1.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C 2.1: 26 percent / tributyltin hydride 3.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 4.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: toluene / 1 h / 0 - 20 °C 1.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C 2.1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating 3.1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating 4.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 5.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: toluene / 1 h / 0 - 20 °C
1.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C
2.1: 26 percent / tributyltin hydride
3.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
4.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme

Multi-step reaction with 5 steps
1.1: toluene / 1 h / 0 - 20 °C
1.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C
2.1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating
3.1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating
4.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
5.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme

: 2043-61-0
cyclohexanecarbaldehyde

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: toluene / Heating 2.1: toluene / 1 h / 0 - 20 °C 2.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C 3.1: 26 percent / tributyltin hydride 4.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 5.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: toluene / Heating 2.1: toluene / 1 h / 0 - 20 °C 2.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C 3.1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating 4.1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating 5.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 6.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: toluene / Heating
2.1: toluene / 1 h / 0 - 20 °C
2.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C
3.1: 26 percent / tributyltin hydride
4.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
5.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme

Multi-step reaction with 6 steps
1.1: toluene / Heating
2.1: toluene / 1 h / 0 - 20 °C
2.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C
3.1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating
4.1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating
5.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
6.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme

: 608532-87-2
4,4,6-trichloro-2-(dimethylamino)-2-azaspiro[4.5]decan-3-one

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; water / ethanol / 110 °C 2: 39 mg / magnesium monoperoxyphthalate hexahydrate / methanol / 3 h / 20 °C View Scheme

: 608532-81-6
1-hydroxy-2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 2: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme

: 608532-79-2
2,2,2-trichloro-N-(cyclohexylidenemethyl)-N-(4-methoxybenzyl)acetamide

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 26 percent / tributyltin hydride 2: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 3: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating 2: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating 3: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 4: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme

: 608532-80-5
1,4,4-trichloro-2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating 2: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 3: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme

: 1-(aminomethyl)cyclohexaneacetic acid hydrochloride

A mother liquor A: mother liquor A

B mother liquor B: mother liquor B

C: 64744-50-9
gabapentin-lactam

D impurity: impurity

E: 60142-96-3
H-Gpn-OH

Conditions

Conditions	Yield
With sodium hydroxide; pyrographite In water at 5 - 75℃; for 8h; Conversion of starting material;

...Expand

: 1-(aminomethyl)cyclohexaneacetic acid hydrochloride

A mother liquor B: mother liquor B

B: 64744-50-9
gabapentin-lactam

C impurity: impurity

D: 60142-96-3
H-Gpn-OH

Conditions

Conditions	Yield
With sodium hydroxide; pyrographite In water at 0 - 70℃; for 6h; Conversion of starting material;
With sodium hydroxide; pyrographite In water at 10 - 80℃; for 11.5h; Conversion of starting material;
With sodium hydroxide; pyrographite In water at 5 - 75℃; for 11.5h; Conversion of starting material;

...Expand

mother liquor A: mother liquor A

mother liquor B: mother liquor B

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
With sodium hydroxide; pyrographite In water at 80 - 85℃; for 2h;

: 460711-33-5
ethyl 2-(1-formylcyclohexyl)acetate

: 64744-50-9
gabapentin-lactam

Conditions

Conditions	Yield
Stage #1: ethyl 2-(1-formylcyclohexyl)acetate With ammonia In ethanol at 20℃; for 48h; Stage #2: With hydrogen; acetic acid; 5%-palladium/activated carbon at 80 - 100℃; under 2844.39 Torr; for 3h; Product distribution / selectivity;

: 64744-50-9
gabapentin-lactam

: 24424-99-5
di-tert-butyl dicarbonate

: 898552-75-5
3-oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap In acetonitrile at 25℃;	92%

: 104-53-0
3-phenyl-propionaldehyde

: 64744-50-9
gabapentin-lactam

: 2-(3-phenylprop-1-en-1-yl)-2-azaspiro[4.5]decan-3-one

Conditions

Conditions	Yield
With acetic acid In toluene at 110℃; for 12h; Dean-Stark;	92%

: 64744-50-9
gabapentin-lactam

: 1-(aminomethyl)cyclohexaneacetic acid hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water at 80 - 90℃; for 5h; Heating / reflux;	90.9%
With hydrogenchloride; water for 24h; Reflux;	90%
With hydrogenchloride; water at 100℃; for 10h;	90%

: 64744-50-9
gabapentin-lactam

: 1809-20-7
diisopropyl hydrogenphosphonate

: 1417780-49-4
diisopropyl(3-oxo-2-azaspiro[4,5]decan-2-yl)phosphonate

Conditions

Conditions	Yield
With copper diacetate; potassium carbonate In toluene at 80℃; under 760.051 Torr; for 0.666667h; Reagent/catalyst; Molecular sieve;	87%

: 64744-50-9
gabapentin-lactam

: 98-59-9
p-toluenesulfonyl chloride

: 2-tosyl-2-azaspiro[4.5]decan-3-one

Conditions

Conditions	Yield
Stage #1: gabapentin-lactam With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	87%

: 64744-50-9
gabapentin-lactam

: 100-51-6
benzyl alcohol

: 2-benzoyl-2-aza-spiro[4.5]decan-3-one

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; 9-azanoradamantane N-oxyl; oxygen; copper(l) chloride In tetrahydrofuran at 23℃; for 1h; Molecular sieve;	87%

: 64744-50-9
gabapentin-lactam

: 106-45-6
para-thiocresol

: 4,4-pentamethylene-N-(p-tolylthio)-2-pyrrolidone

Conditions

Conditions	Yield
With potassium fluoride; oxygen In 1,3,5-trimethyl-benzene at 100℃; under 760.051 Torr; for 1h; Autoclave;	76%

: 64744-50-9
gabapentin-lactam

: 70-55-3
toluene-4-sulfonamide

: 4-methyl-N-(2-azaspiro[4.5]decan-3-ylidene)benzenesulfonamide

Conditions

Conditions	Yield
With diazoacetic acid ethyl ester; manganese(II) perchlorate hexahydrate In cyclohexane at 90℃; for 12h; chemoselective reaction;	72%

: 64744-50-9
gabapentin-lactam

: 13574-13-5
Boc-Glu(OBzl)-OH

: benzyl (S)-4-((tert-butoxycarbonyl)amino)-5-oxo-5-(3-oxo-2-azaspiro[4.5]decan-2-yl)pentanoate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 5h;	60%

: 64744-50-9
gabapentin-lactam

: 797762-15-3
1-aminomethyl-1-cyclohexaneacetic acid hydrobromide

Conditions

Conditions	Yield
With water; hydrogen bromide at 0 - 114℃; for 6 - 24h; Product distribution / selectivity; Heating / reflux;	59.27%
With water; hydrogen bromide at 0 - 114℃; for 24 - 45h; Product distribution / selectivity; Heating / reflux;	59.27%

: 4530-20-5
BOC-glycine

: 64744-50-9
gabapentin-lactam

: tert-butyl (2-oxo-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)ethyl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 5h;	57%

: 64744-50-9
gabapentin-lactam

: 591-50-4
iodobenzene

: 2-phenyl-2-azaspiro[4.5]decan-3-one

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; 1,3-bis(methylamino)propane In 1,4-dioxane for 24h; Reflux;	50%

Gabapentin-lactam Specification

The Gabapentin-lactam, with the CAS registry number 64744-50-9, is also known as beta,beta-Pentamethylen-gamma-butyrolactam. It belongs to the product categories of Intermediates of Gabapentin; (Intermediate of gabapentin); Heterocyclic Compounds; Intermediates & Fine Chemicals; Neurochemicals; Pharmaceuticals. This chemical's molecular formula is C₉H₁₅NO and molecular weight is 153.2215. Its IUPAC name is called 3-azaspiro[4.5]decan-2-one. This chemical's classification code is Drug / Therapeutic Agent. This chemical is white solid which reduces protein aggregates and improves motor performance in a transgenic mouse model of Huntington disease. What's more, this chemical opens mitochondrial ATP-dependent potassium channels. When you are using this chemical, please be cautious about it. You should not breathe its dust. In addition, you must avoid contacting it with skin and eyes.

Physical properties of Gabapentin-lactam: (1)ACD/LogP: 0.62; (2)ACD/LogD (pH 5.5): 0.62; (3)ACD/LogD (pH 7.4): 0.62; (4)ACD/BCF (pH 5.5): 1.76; (5)ACD/BCF (pH 7.4): 1.76; (6)ACD/KOC (pH 5.5): 52.07; (7)ACD/KOC (pH 7.4): 52.07; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Index of Refraction: 1.509; (11)Molar Refractivity: 43.4 cm³; (12)Molar Volume: 145.2 cm³; (13)Surface Tension: 38.1 dyne/cm; (14)Density: 1.05 g/cm³; (15)Flash Point: 192.3 °C; (16)Enthalpy of Vaporization: 57.27 kJ/mol; (17)Boiling Point: 330.1 °C at 760 mmHg; (18)Vapour Pressure: 0.000169 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1CCC2(CC1)CC(=O)NC2
(2)InChI: InChI=1S/C9H15NO/c11-8-6-9(7-10-8)4-2-1-3-5-9/h1-7H2,(H,10,11)
(3)InChIKey: JAWPQJDOQPSNIQ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	intravenous	125mg/kg (125mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 243, 1960.

Product Name

Gabapentin-lactam

Synthetic route

Gabapentin-lactam Specification

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