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Chemical Structure| 24666-56-6 Chemical Structure| 24666-56-6

Structure of 24666-56-6

Chemical Structure| 24666-56-6

3-Aminopiperidine-2,6-dione HCl

CAS No.: 24666-56-6

4.5 *For Research Use Only !

Cat. No.: A476158 Purity: 97%

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Product Details of [ 24666-56-6 ]

CAS No. :24666-56-6
Formula : C5H9ClN2O2
M.W : 164.59
SMILES Code : O=C(C(N)CC1)NC1=O.[H]Cl
MDL No. :MFCD11042437
InChI Key :YCPULGHBTPQLRH-UHFFFAOYSA-N
Pubchem ID :134548

Safety of [ 24666-56-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 24666-56-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 0.6
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 40.82
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

72.19 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.69
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.83
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.55
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.19
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.45

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.43
Solubility 61.8 mg/ml ; 0.375 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.35
Solubility 73.3 mg/ml ; 0.445 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.47
Solubility 55.9 mg/ml ; 0.34 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.79 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.71

Application In Synthesis of [ 24666-56-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 24666-56-6 ]

[ 24666-56-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 24666-56-6 ]
  • [ 133446-99-8 ]
  • 3-(5-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With triethylamine; In N,N-dimethyl-formamide; at 75℃; for 12h; To a solution of 3-aminopiperidine-2,6-dione (2.00 g, 12.2 mmol, HCl) and <strong>[133446-99-8]methyl 2-(bromomethyl)-4-nitro-benzoate</strong> (4.21 g, 15.4 mmol) in DMF (10.0 mL) was added TEA (3.07 g, 30.4 mmol). The reaction mixture was stirred at 75 C. for 12 hrs. On completion, the reaction mixture was diluted with water (200 mL), filtered. The filtered cake was collected. The reaction mixture was concentrated in vacuo. The residue was triturated EA:H2O=1:1 (50 mL) to give the title compound (1.7 g, 48% yield) as a blue solid. 1H NMR (400 MHz, DMSO-d6) delta 11.04 (s, 1H), 8.53 (d, J=1.2 Hz, 1H), 8.36 (dd, J=2.0, 8.4 Hz, 1H), 7.98 (d, J=8.4 Hz, 1H), 5.17 (dd, J=5.2, 13.2 Hz, 1H), 4.69-4.45 (m, 1H), 3.01-2.86 (m, 1H), 2.68-2.59 (m, 1H), 2.48-2.35 (m, 1H), 2.13-2.02 (m, 1H).
1.50 g With potassium carbonate; In N,N-dimethyl-formamide; at 25 - 45℃; for 6h; Preparation of <strong>[133446-99-8]methyl <strong>[133446-99-8]2-(bromomethyl)-4-nitrobenzoate</strong></strong> (23-1) (2.5 g, 9.12 mmol) and 3- aminopiperidine-2,6-dione (1-2) (1.74 g, 13.6 mmol) were added to DMF (12.5 ml) at 25C. Potassium carbonate (3.15 g, 22.8 mmol) was added to the reaction mixture at 25C and the temperature was raised to 42C. The reaction mixture was stirred for 6 hours at 42C and cooled to 20C to 25C. De-ionized water (12.5 ml) was added to the reaction mixture at 20C and stirred for 20 minutes. The solid obtained was filtered, washed with de-ionized water (2 x 25 ml) and dried under vacuum at 40C to 45C for 20 hours to obtain the title compound.Then the crude material was slurried with PE/EA(1/1) 20 mL to give 3-(5-nitro-1-oxoisoindolin-2-yl)piperidine- 2,6-dione (23-2) (1.50 g, 5.18 mmol, ) as gray-green solid. LC/MS (ES+): m/z 290 [M + H]+
  • 3
  • [ 24666-56-6 ]
  • [ 6946-22-1 ]
  • [ 19171-19-8 ]
YieldReaction ConditionsOperation in experiment
94% Example 14; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; Example 14 was prepared similarly according to the procedure for Example 13 except that there was no acetic acid; the amount of triethylamine was reduced from 4.6 mol to 3.2 mol; and the refluxing time was increased from about 5 to 7 hours to about 47 hours. The amount of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione in the reaction mixture was found to be 94percent.
92% Example 15; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; Example 15 was prepared similarly according to the procedure for Example 13 except that there was no acetic acid and the 4.6 mol of triethylamine was replaced with 9.2 mole of imidazole. The amount of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione in the reaction mixture was found to be 92percent
85% Example 16; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; Example 16 was prepared similarly according to the procedure for Example 13 except that the 4.6 mol of triethylamine was replaced with 9.2 mole of imidazole. The amount of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione in the reaction mixture was found to be 85percent.
84% Example 13; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; According to Scheme E A mixture of <strong>[6946-22-1]<strong>[6946-22-1]3-aminophthalic acid</strong> hydrochloride</strong> (200 g, 0.92 mol, from Prosynth Ltd., Suffolk, UK), 3-aminoglutarimide hydrochloride (159 g, 0.96 mol, from Evotec OAI, Hamburg, Germany), acetonitrile (2.0 L), and acetic acid (577 g, 9.6 mol, from Fisher Scientifc) was charged into a reaction vessel. After the mixture was stirred for 15 minutes, triethylamine (465.0 g, 4.6 mol, from Aldrich, Milwaukee, Wis.) was added dropwise over 30-35 minutes while the reaction temperature was maintained at 20-25° C. Next, the reaction mixture was stirred further for 10-15 minutes and then refluxed at about 85 to 87° C. for about 5 to 7 hours or until the in-process control, i.e., HPLC AP at 240 nm, indicates that <2percent of the <strong>[6946-22-1]3-aminophthalic acid</strong> remained in the reaction mixture. After the reaction mixture was cooled to about 20 to 25° C. over 1-2 hours, 1.0 L of water was charged over 15-30 minutes at about 20 to 25° C. The resulting mixture was stirred at about 15 to 20° C. for about 20 to 30 minutes to provide a yellow solid precipitate, which was filtered, washed with DI water (3.x.1.0 L) and acetonitrile (2.x.500 mL), and then dried at about 35 to 40° C in vacuo to a constant weight at 210.0 g (84 percent).
68.5% With acetic acid; triethylamine; In acetone; at 80 - 85℃; for 6h; Acetonitrile (100 mL), acetic acid (26.28 mL, 459.5 mmol),Triethylamine (31.85 mL, 229.8 mmol), <strong>[6946-22-1]<strong>[6946-22-1]3-aminophthalic acid</strong> hydrochloride</strong> (10 g, 46.0 mmol),Aminopiperidine-2,6-dione hydrochloride (7.68 g, 46.6 mmol)Added to the reaction flask, heated to 80 ~ 85 ° C reflux, the reaction was complete after 6h,The reaction solution was cooled to 20 ~ 25 ° C, purified water was slowly added, the crystallization was stirred for 2h, filtered, the filter cake was dried under reduced pressure at 60 ± 5 ° C for 8h to obtain 8.6g black solid, yield 68.5percent

  • 4
  • [ 652-12-0 ]
  • [ 24666-56-6 ]
  • 2-[(2,6-dioxo-3-piperidinyl)amino]carbonyI}-3,4,5,6-tetrafluorobenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Triethylamine (0.65 mi, 4.54 mmol) was added to a suspension of 16 (0.37 g, 2.27 mmol) in dry tetrahydrofuran (40 ml) and the mixture was stirred at room temperature for 10 min. Tetrafluorophthalic anhydride (17) (0.50 g, 2.27 mmol) was added and stirring was continued at room temperature for 48 h. The reaction mixture was partitioned between ethyl acetate and water and the aqueous portion was acidified with 2N HCl and extracted with ethyl acetate (5 times). The combined extracts were worked up to give an oil which was dried well in vacuo and then triturated with diethyl ether until crystallization began. The solid was filtered off and further triturated with cold diethyl ether (5 times) to give the title compound 2 as a white powder (0.54 g, 62%), mp 254-258 0C. 1H NMR (400 MHz, DMSO-D6) δ ppm 14.00 (br, IH), 10.85 (s, IH, exch. with D2O), 9.08 (d, J=8.0 Hz, IH, exch. with D2O), 4.75-4.69 (m, IH), 2.79-2.69 (m, <n="15"/>IH), 2.58-2.48 (m, IH), 2.08-2.00 (m, IH)5 1.99-1.90 (m, IH). Found: C, 44.71; H, 2.43; N3 7.82. C13H8F4N2O5 requires C, 44.84; H, 2.32; N, 8.05%.
  • 5
  • [ 188187-03-3 ]
  • [ 24666-56-6 ]
  • [ 1198299-48-7 ]
  • 6
  • [ 73721-78-5 ]
  • [ 24666-56-6 ]
  • [ 1620018-94-1 ]
YieldReaction ConditionsOperation in experiment
35% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; at 20.0℃; for 24.0h;Inert atmosphere; Step 3. Synthesis of rac-2-Acetamido-N-(2,6-dioxopiperidin-3-yi)-6-nitrobenzamide [00302] The starting acid (3.10 g, 13.8 mmol) was mixed with hydroxybenzotriazole (HOBt, 2.12 g of the hydrate, 13.8 mmol) and l-ethyl-3-(3-dimethylaminopropyl)- carbodiimide hydrochloride (EDC, 2.54 g, 13.3 mmol), under a nitrogen atmosphere. N,N- dimethylformamide (DMF, 21.4 mL) was added and the mixture was stirred for 30 minutes at room temperature. rac-3-Aminopiperidine-2,6-dione hydrochloride (5.01 g, 30.4 mmol) was added, followed by Nu,Nu-diisopropylethylamine (DIEA, 9.63 mL, 55.3 mmol). The reaction mixture was stirred at 20C, while monitoring by HPLC. After 24 hours, the reaction mixture showed approximately 40% conversion to the desired product containing some remaining starting acid, but no amine. Then, the reaction mixture was slowly poured into 200 mL water with vigorous stirring. After 20 minutes, a white precipitate began to form. The mixture was placed in the refrigerator for 18 hours. Then, the precipitate was isolated by filtration. The filter cake was washed with 50 mL ether, and air dried to provide the title compound (1.60 g, 4.79 mmol, 35%) as a white powder. XH NMR (300 MHz, DMSO-d6) delta 1 1.16 (s, 1H), 9.40 (s, 1H), 9.34 (d, J = 8.0 Hz, 1H), 8.53 (d, J = 7.5 Hz, 1H), 7.89 (dd, J = 8.2, 0.98 Hz, 1H), 7.66 (t, J = 8.3 Hz, 1H), 4.79 (m, 1H), 2.85(m, 1H), 2.59 (m, 1H), 2.21 (m, 1H), 2.20 (s, 3H), 2.03 (m, 1H). MS (ESI-) calc. for [Ci4H14N406-H]" 333.3, found 333.2.
  • 7
  • [ 652-40-4 ]
  • [ 24666-56-6 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4,7-difluoroisoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium acetate; acetic acid; at 120℃; for 16h; 3,6-Difluorophthalic anhydride (77.3 mg, 0.40 mmol, 1.0 eq.), potassium acetate (120.8 mg, 1.24 mmol, 3.1 eq.), and 3-aminopiperidine-2,6-dione hydrochloride (80.4 mg, 0.48 mmol, 1.2 eq.) were dissolved in glacial acetic acid (1.2 mL, 0.33 M), and then the mixture was heated to 120 C. After 16 hours, the reaction was cooled to room temperature and the excess acetic acid was removed by rotary evaporation. The residue was dissolved in EtOAc and water (20 mL each), and the aqueous layer was extracted 4 times with EtOAc (15 mL). The combined organic layers were washed with water and then brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide the desired product as a tan solid (94.0 mg, 80% yield). NMR: (500 MHz, DMSO-i) delta 11.14 (s, 1H), 7.79 (t, J= 5.7 Hz, 2H), 5.15 (dd, J = 12.9, 5.4 Hz, 1H), 2.88 (ddd, J = 17.1, 13.8, 5.5 Hz, 1H), 2.60 (d, J = 17.3 Hz, 1H), 2.55 - 2.45 (m, 1H), 2.05 (m, 1H).MS: 295.17 (M+H)+.
  • 8
  • [ 120550-35-8 ]
  • [ 24666-56-6 ]
  • N-(2,6-dioxopiperidin-3-yl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide [ No CAS ]
  • 9
  • [ 165111-46-6 ]
  • [ 24666-56-6 ]
  • [ 1010100-27-2 ]
YieldReaction ConditionsOperation in experiment
22% [0132] To a solution of 3 -amino-2, 6-piperidinedi one HC1 (648 mg, 3.94 mmol) in DMF (20 mL) at RT was added TEA (1.21 mL, 8.67 mmol) and stirred for 10 min. The mixture was cooled to 0 C then a solution of <strong>[165111-46-6]methyl 2-(bromomethyl)-4-cyanobenzoate</strong> (1.00 g, 3.94 mmol) in DMF was added dropwise. After 10 min, the reaction was warmed to RT and stirred for 2 days then concentrated. The residue was purified by silica gel chromatography eluting with hexanes/EA (1 : 1) to hexanes (100%) to give 2-(2,6-dioxo-3-piperidyl)-l-oxo-5- isoindolinecarbonitrile (230 mg, 22% yield) as a solid. LCMS (ESI) m/z 270 [M+H] +.
  • 10
  • [ 652-12-0 ]
  • [ 24666-56-6 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4,5,6,7-tetrafluoroisoindoline-1,3-dione, [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium acetate; acetic acid; for 3h;Reflux; To a round bottom flask was added tetrafluorophthalic anhydride (1.65 g, 7.5 mmol) and 3-aminopiperidine-2,6-dione hydrochloride (0.82 g, 5.0 mmol). A solution of sodium acetate (0.5 g, 6.0 mmol) in glacial acetic acid (20 mL) was added and the colorless solution was refluxed for 3 h. After cooling, the purple suspension was filtered, and H2O (50 mL) was added to the filtrate. The colorless solid formed was collected, washed with H2O (3×5 mL) and petroleum ether (3×5 mL) and it was further dried in vacuo to give the title product as a colorless solid. Yield (1.13g, 68%); mp 238-240 C; 1H NMR (500 MHz, DMSO-d6) δ 2.01-2.11 (m, 1H), 2.41-2.65 (m, 2H), 2.82-2.93 (m, 1H), 5.18 (dd, J=5.4, 13.0Hz, 1H), 11.15 (br s, 1H); 13C NMR (126 MHz, DMSO-d6) δ 21.78, 30.95, 49.69, 113.52 (d, 3J (C,F)=8.3 Hz), 142.72 (m, 1J (C,F)=266Hz), 145.14 (m, 1J (C,F)=264Hz); 161.98, 169.31, 172.68; LC-MS (ESI) 99% purity, m/z [M+NH4]+ calcd for C13H6F4N2O4, 348.06; found, 348.1; HRMS m/z [M - H]- calcd for C13H6F4N2O4, 329.0191; found, 329.0201.
 

Historical Records

Categories

Related Functional Groups of
[ 24666-56-6 ]

Amides

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Amines

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Related Parent Nucleus of
[ 24666-56-6 ]

Piperidines

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