3-Amino-2,6-piperidinedione hydrochloride supplier

Name
2,6-Dioxopiperidine-3-ammonium chloride
EINECS 807-866-6
CAS No. 24666-56-6
Article Data9
CAS DataBase
Density
Solubility
Melting Point 120 °C (approx)
Formula C₅H₉ClN₂O₂
Boiling Point 334.5 °C at 760 mmHg
Molecular Weight 164.592
Flash Point 156.1 °C
Transport Information
Appearance
Safety 3/9-36/37
Risk Codes 20/21/22
Molecular Structure
Hazard Symbols
Synonyms 2,6-Piperidinedione,3-amino-, monohydrochloride (9CI);Glutarimide, 2-amino-, hydrochloride(6CI,7CI);Glutarimide, 2-amino-, monohydrochloride (8CI);3-Amino-2,6-dioxopiperidine hydrochloride;3-Aminopiperidine-2,6-dione monohydrochloride;DL-Glutamic acidimide hydrochloride;Glutamimide hydrochloride;
PSA 72.19000
LogP 0.58140

Synthetic route

: 24666-55-5
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; 5% palladium over charcoal In methanol; water under 3102.97 Torr; for 4h;	100%
With hydrogenchloride In dimethyl sulfoxide	92%
Stage #1: 3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine With palladium 10% on activated carbon; hydrogen In methanol; water at 25 - 30℃; under 2250.23 - 2625.26 Torr; Stage #2: With hydrogenchloride In methanol; water at 25 - 30℃;	90%
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 5h;	90.5%
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethyl acetate under 2585.74 - 3102.89 Torr;

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water for 2h;	99%

: N-(2,6-dioxopiperidin-3-yl)-2-phenylacetamide

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol under 760.051 Torr; for 23h;	96%

: 617-65-2
Glutamic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
Stage #1: Glutamic acid With ammonium hydroxide In water at 15℃; for 0.5h; Stage #2: In water at 60℃; for 2h; Stage #3: With hydrogenchloride In ethanol at 30℃; Temperature;	82.6%

<(S)-2,6-dioxo-<3>piperidyl>-carbamic acid benzyl ester: <(S)-2,6-dioxo-<3>piperidyl>-carbamic acid benzyl ester

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; palladium Hydration;

: 2650-64-8
Cbz-L-Gln

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CDI / tetrahydrofuran / Heating 2: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr View Scheme
Multi-step reaction with 2 steps 1: dmap; 1,1'-carbonyldiimidazole / 1,4-dioxane / 15 h / 100 °C 2: palladium 10% on activated carbon; hydrogen; hydrogenchloride / methanol / 5 h / 25 °C View Scheme

: 6398-06-7
N-benzyloxycarbonyl-L-isoglutamine

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1,1'-carbonyldiimidazole / tetrahydrofuran / 20 h / Reflux 2: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 23 h / 760.05 Torr View Scheme

: 56-86-0
L-glutamic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: water / 2 h / 0 °C 2: urea / dimethyl sulfoxide / 2 h / 150 °C 3: hydrogenchloride / dimethyl sulfoxide View Scheme

: 1155-62-0
N-benzyloxycarbonyl-L-glutamic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: urea / dimethyl sulfoxide / 2 h / 150 °C 2: hydrogenchloride / dimethyl sulfoxide View Scheme

: 50516-14-8
Nα-benzyloxycarbonyl-glutamine

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1,1'-carbonyldiimidazole / 1,4-dioxane / 17.17 h / 20 °C / Heating / reflux 2: hydrogenchloride; hydrogen / 5% palladium over charcoal / methanol; water / 4 h / 3102.97 Torr View Scheme

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 827026-45-9
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions

Conditions	Yield
Stage #1: rac-α-aminoglutarimide hydrochloride With triethylamine In dimethyl sulfoxide for 0.166667h; Inert atmosphere; Stage #2: 2-bromomethyl-3-nitro-benzoic acid methyl ester In dimethyl sulfoxide at 50 - 55℃; for 12.3333h; Inert atmosphere;	99.73%
With sodium carbonate at 100℃; for 0.75h; Reagent/catalyst; Temperature; Inert atmosphere;	98.5%
With sodium carbonate In acetonitrile at 70℃; for 8h; Solvent; Reagent/catalyst; Temperature;	98.8%

: 82-73-5
3-bromophthalic anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 4-bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With potassium acetate; acetic acid at 90℃; for 16h;	99%
With potassium acetate; acetic acid at 90℃; for 16h; Inert atmosphere;	99%
With sodium acetate; acetic acid for 3h; Reflux;	94.1%

: 4-[4,4-difluoro-5-[4-[3-[[5-(5-methylpyrido[4,3-b]indol-7-yl)-2-pyridyl]oxy]cyclobutoxy]-1-piperidyl]pentoxy]phthalic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 5-[4,4-difluoro-5-[4-[3-[[5-(5-methylpyrido[4,3-b]indol-7-yl)-2-pyridyl]oxy]cyclobutoxy]-1-piperidyl]pentoxy]-2-(2,6-dioxo-3-piperidyl)isoindolin-1,3-dione

Conditions

Conditions	Yield
Stage #1: 4-[4,4-difluoro-5-[4-[3-[[5-(5-methylpyrido[4,3-b]indol-7-yl)-2-pyridyl]oxy]cyclobutoxy]-1-piperidyl]pentoxy]phthalic acid With sodium acetate; acetic acid at 25℃; for 1h; Stage #2: rac-α-aminoglutarimide hydrochloride at 120℃; for 11h;	98%

: 15371-06-9
3-acetylaminophthalic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 444289-17-2
N-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)acetamide

Conditions

Conditions	Yield
With potassium acetate In 1,4-dioxane at 100℃; for 24h; Reagent/catalyst; Solvent; Temperature;	97.5%

: 37418-88-5
3-hydroxyphthalic anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 5054-59-1
4-Hydroxythalidomide

Conditions

Conditions	Yield
With potassium acetate In acetic acid for 24h; Reflux;	96%
With sodium acetate; acetic acid at 100℃; for 2h;	96%
With pyridine at 110℃;	93%

: 319-03-9
4-fluorophthalic anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 835616-61-0
2-(2,6-dioxopiperidin-3-yl)-5-fluoro-2,3-dihydro-1H-isoindole-1,3-dione

Conditions

Conditions	Yield
With sodium acetate; acetic acid at 120℃; for 12h;	96%
With sodium acetate; acetic acid at 135℃;	92%
With sodium acetate In acetic acid for 12h; Reflux;	90%

: benzyl (4-(2-((1,3-dioxo-1,3-dihydroisobenzofuran-4-yl)oxy)acetamido)butyl)carbamate

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: benzyl (4-(2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)acetamido)butyl)carbamate

Conditions

Conditions	Yield
Stage #1: benzyl (4-(2-((1,3-dioxo-1,3-dihydroisobenzofuran-4-yl)oxy)acetamido)butyl)carbamate; rac-α-aminoglutarimide hydrochloride With triethylamine In tetrahydrofuran for 3h; Reflux; Inert atmosphere; Stage #2: With 1,1'-carbonyldiimidazole In tetrahydrofuran Reflux; Inert atmosphere;	96%

: 85-44-9
phthalic anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 50-35-1
thalidomide

Conditions

Conditions	Yield
With acetic acid; triethylamine for 3h; Temperature; Reagent/catalyst; Concentration; Reflux;	95%

: 6296-53-3
3-acetylaminophthalic anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 444289-17-2
N-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)acetamide

Conditions

Conditions	Yield
With sodium acetate; acetic acid at 105℃; for 24h; Reagent/catalyst; Temperature;	95%

: 23204-36-6
3-hydroxy-1,8-naphthalic acid anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 2-(2,6-dioxopiperidin-3-yl)-5-hydroxy-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 120h; Reflux;	95%
With triethylamine In tetrahydrofuran for 120h; Reflux;	3.44 g

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 6946-22-1
3-aminophthalic acid hydrochloride

: 19171-19-8
pomalidomide

Conditions

Conditions	Yield
Stage #1: rac-α-aminoglutarimide hydrochloride; 3-aminophthalic acid hydrochloride In acetonitrile for 0.25h; Stage #2: With triethylamine In water; acetonitrile at 15 - 87℃; for 49.0833 - 50.8333h; Product distribution / selectivity;	94%
Stage #1: rac-α-aminoglutarimide hydrochloride; 3-aminophthalic acid hydrochloride In acetonitrile for 0.25h; Stage #2: With 1H-imidazole In water; acetonitrile at 15 - 87℃; for 7.08333 - 10.8333h; Product distribution / selectivity;	92%
Stage #1: rac-α-aminoglutarimide hydrochloride; 3-aminophthalic acid hydrochloride With acetic acid In acetonitrile for 0.25h; Stage #2: With 1H-imidazole In water; acetonitrile at 15 - 87℃; for 7.08333 - 10.8333h; Product distribution / selectivity;	85%
Stage #1: rac-α-aminoglutarimide hydrochloride; 3-aminophthalic acid hydrochloride With acetic acid In acetonitrile for 0.25h; Stage #2: With triethylamine In water; acetonitrile at 15 - 87℃; for 7.08333 - 10.8333h; Product distribution / selectivity;	84%
With acetic acid; triethylamine In acetone at 80 - 85℃; for 6h;	68.5%

: 18959-30-3
4,5-difluorophthalic anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 2-(2,6-dioxopiperidin-3-yl)-5,6-difluoroisoindoline-1,3-dione

Conditions

Conditions	Yield
With potassium acetate; acetic acid at 90℃;	94%
With potassium acetate; acetic acid at 110℃;
With triethylamine In toluene at 100℃; for 4h;

: methyl 2-(chloromethyl)-3-nitrobenzoate

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 827026-45-9
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 80℃; for 10h;	93.2%

: 86-90-8
4-bromophthalic anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 26166-92-7
5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Conditions

Conditions	Yield
With sodium acetate; acetic acid Heating / reflux;	93%
With sodium acetate In acetic acid at 20 - 80℃; for 16h;	92%
With sodium acetate; acetic acid at 115℃; for 16h;	91.6%
With potassium acetate; acetic acid at 90℃; for 12h;	60%
With sodium acetate; acetic acid at 120℃; for 5h;

: 927672-71-7
C20H15NO5

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 927671-10-1
4-(2-phenoxyphenylamino)-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione

Conditions

Conditions	Yield
With pyridine for 16h; Heating / reflux;	93%

: 927672-50-2
3-(4-tert-butylphenylamino)phthalic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 927670-99-3
4-(4-tert-butylphenylamino)-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione

Conditions

Conditions	Yield
With pyridine for 16h; Heating / reflux;	92%

: 927672-63-7
3-(naphthalen-2-ylamino)phthalic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 927671-06-5
2-(2,6-Dioxopiperidin-3-yl)-4-(naphthalen-2-ylamino)isoindole-1,3-dione

Conditions

Conditions	Yield
With pyridine for 16h; Heating / reflux;	92%

: 927672-67-1
3-(2-methoxyphenylamino)phthalic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 927671-08-7
4-(2-Methoxyphenylamino)-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione

Conditions

Conditions	Yield
With pyridine for 16h; Heating / reflux;	92%

: 652-39-1
3-fluorophthalic anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 2‐(2,6‐dioxopiperidin‐3‐yl)‐4‐fluoroisoindoline‐1,3‐dione

Conditions

Conditions	Yield
With sodium acetate; acetic acid at 135℃;	92%
With sodium acetate; acetic acid for 12h; Reflux;	90%
With sodium acetate In acetic acid for 12h; Reflux;	90%

: 1477-50-5
Indole-2-carboxylic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: N-(2,6-dioxopiperidin-3-yl)-1H-indole-2-carboxamide

Conditions

Conditions	Yield
Stage #1: Indole-2-carboxylic acid 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 20℃; for 1h; Inert atmosphere; Stage #2: rac-α-aminoglutarimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	92%

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 2-chloropyridine-3,4-dicarboxylic acid

: 4-chloro-2-(2,6-dioxopiperidin-3-yl)-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione

Conditions

Conditions	Yield
With 1,1'-carbonyldiimidazole In acetonitrile for 16h;	91.7%
With 1,1'-carbonyldiimidazole In acetonitrile at 80℃; for 16h; Inert atmosphere;	27%

: 641-70-3
3-nitrophthalic acid anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 2-((2,6-dioxopiperidin-3-yl)carbamoyl)-3-nitrobenzoic acid

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Reagent/catalyst; Green chemistry;	91%
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;	91%
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;	91%

: 603-11-2
3-nitrophthalic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 19171-18-7
4-NT

Conditions

Conditions	Yield
With sodium acetate; acetic acid at 105 - 115℃; Large scale;	90%
With sodium acetate; acetic acid In water at 116 - 118℃; for 16h;	86.2%
With 1,1'-carbonyldiimidazole In acetonitrile at 20 - 80℃; Inert atmosphere;	28.2 g

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: N-(2,6-dioxopiperidin-3-yl)-2-nitrobenzenesulfonamide

Conditions

Conditions	Yield
Stage #1: rac-α-aminoglutarimide hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-Nitrobenzenesulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃;	90%

: 88-67-5
2-Iodobenzoic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: N-(2,6-dioxopiperidin-3-yl)-2-iodobenzamide

Conditions

Conditions	Yield
Stage #1: 2-Iodobenzoic acid 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 for 0.166667h; Stage #2: rac-α-aminoglutarimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h;	90%
Stage #1: 2-Iodobenzoic acid 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 20℃; for 1h; Inert atmosphere; Stage #2: rac-α-aminoglutarimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	73%

: 641-70-3
3-nitrophthalic acid anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 19171-18-7
4-NT

Conditions

Conditions	Yield
With sodium acetate; acetic acid at 25 - 118℃; for 18h;	89.7%
With formic acid; ammonium formate at 80℃; for 0.166667h; Temperature;	89%
With sodium acetate; acetic acid In water at 116 - 118℃; for 17h;	88.3%

: 927672-52-4
3-(4-isopropylphenylamino)phthalic acid

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 927671-00-9
4-(4-isopropylphenylamino)-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione

Conditions

Conditions	Yield
With pyridine for 16h; Heating / reflux;	89%

3-Amino-2,6-piperidinedione hydrochloride Specification

The 3-Amino-2,6-piperidinedione hydrochloride with the cas number 24666-56-6 is also called 2,6-Piperidinedione,3-amino-, hydrochloride (1:1). Its molecular formula is C₅H₉ClN₂O₂. This chemical should be stored in dry and cool environment.

The properties of the chemical are: (1)ACD/LogP: -1.05; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.31; (4)ACD/LogD (pH 7.4): -1.14; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 5.22; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 40.62 Å²; (13)Enthalpy of Vaporization: 57.74 kJ/mol; (14)Vapour Pressure: 0.000128 mmHg at 25°C.

Uses: This chemical can react with 2-bromo-benzoyl chloride to prepare 2-bromo-N-(2,6-dioxo-piperidin-3-yl)-benzamide. This reaction needs reagent aq. Na₂CO₃ and solvent dioxane at temperature of 0 - 20 °C. The yield is 53%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1NC(=O)C(N)CC1.Cl
(2)InChI: InChI=1/C5H8N2O2.ClH/c6-3-1-2-4(8)7-5(3)9;/h3H,1-2,6H2,(H,7,8,9);1H
(3)InChIKey: YCPULGHBTPQLRH-UHFFFAOYAG

Product Name

2,6-Dioxopiperidine-3-ammonium chloride

Synthetic route

3-Amino-2,6-piperidinedione hydrochloride Specification

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