Product Name

  • Name

    Carbamic acid, (2,6-dioxo-3-piperidinyl)-, phenylmethyl ester (9CI)

  • EINECS
  • CAS No. 24666-55-5
  • Article Data16
  • CAS DataBase
  • Density 1.31g/cm3
  • Solubility
  • Melting Point 129-131 °C(Solv: isopropanol (67-63-0))
  • Formula C13H14 N2 O4
  • Boiling Point 520.2°C at 760 mmHg
  • Molecular Weight 262.265
  • Flash Point 268.4°C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 24666-55-5 (Carbamic acid, (2,6-dioxo-3-piperidinyl)-, phenylmethyl ester (9CI))
  • Hazard Symbols
  • Synonyms 3-Piperidinecarbamicacid, 2,6-dioxo-, benzyl ester (6CI,7CI,8CI); Carbamic acid, (2,6-dioxo-3-piperidinyl)-,phenylmethyl ester (9CI)
  • PSA 84.50000
  • LogP 1.43770

Synthetic route

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

N-benzyloxycarbonyl-L-glutamic acid

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

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

Conditions
ConditionsYield
With urea In dimethyl sulfoxide at 150℃; for 2h; Solvent; Temperature;92%
Nα-benzyloxycarbonyl-glutamine
50516-14-8

Nα-benzyloxycarbonyl-glutamine

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

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

Conditions
ConditionsYield
With dmap; 1,1'-carbonyldiimidazole In 1,4-dioxane at 20℃; for 17.1667h; Heating / reflux;86%
Cbz-L-Gln
2650-64-8

Cbz-L-Gln

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

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide at -5℃; for 3h;81%
With 1,1'-carbonyldiimidazole In ethyl acetate at 76 - 80℃;80%
With 1,1'-carbonyldiimidazole In tetrahydrofuran Heating;
N2-benzyloxycarbonyl-L-glutamine methyl ester
13907-82-9, 2650-67-1

N2-benzyloxycarbonyl-L-glutamine methyl ester

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

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

Conditions
ConditionsYield
With sodium methylate; benzyl alcohol
L-glutamic acid
56-86-0

L-glutamic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

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

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water / 2 h / 0 °C
2: urea / dimethyl sulfoxide / 2 h / 150 °C
View Scheme
L-glutamine
56-85-9

L-glutamine

benzyl chloroformate
501-53-1

benzyl chloroformate

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

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; toluene / 25 - 30 °C / pH 11 - 12
2: 1,1'-carbonyldiimidazole / ethyl acetate / 76 - 80 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

rac-α-aminoglutarimide hydrochloride
24666-56-6

rac-α-aminoglutarimide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; 5% palladium over charcoal In methanol; water under 3102.97 Torr; for 4h;100%
With hydrogenchloride In dimethyl sulfoxide92%
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;
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

3-aminopiperidine-2,6-dione hydrobromide
90802-45-2

3-aminopiperidine-2,6-dione hydrobromide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 20℃; for 2h;97%
With hydrogen bromide In acetic anhydride at 50℃; for 0.75h;96%
With hydrogen bromide; acetic acid at 60℃; for 1h;95.2%
With hydrogen bromide In nitromethane92%
o-azidobenzoyl chloride
34897-85-3

o-azidobenzoyl chloride

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

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

[1-(2-azidobenzoyl)-2,6-dioxo-piperidin-3-yl]carbamic acid benzyl ester

[1-(2-azidobenzoyl)-2,6-dioxo-piperidin-3-yl]carbamic acid benzyl ester

Conditions
ConditionsYield
Stage #1: 3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 0.5h;
Stage #2: o-azidobenzoyl chloride In tetrahydrofuran at 20℃;		52%
benzaldehyde
100-52-7

benzaldehyde

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

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

2-(Benzylideneamino)glutarimide
73839-05-1

2-(Benzylideneamino)glutarimide

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal 1) THF, 12h 1 at H2 2) 3h room temperature; Yield given. Multistep reaction;
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

4-(2-aminoethoxy)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
390367-50-7

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 97 percent / aq. HBr; AcOH / 2 h / 20 °C
2.1: dimethylformamide / 24 h / 60 °C
2.2: 71 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / dimethylformamide / 54 h / 63 °C
3.1: tetraethylammonium fluoride / 72 h / 20 °C
4.1: 34 percent / TFA / CH2Cl2 / 0.75 h / 20 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

(R)-4-(2-aminoethoxy)-thalidomide

(R)-4-(2-aminoethoxy)-thalidomide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 97 percent / aq. HBr; AcOH / 2 h / 20 °C
2.1: dimethylformamide / 24 h / 60 °C
2.2: 71 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / dimethylformamide / 54 h / 63 °C
3.1: tetraethylammonium fluoride / 72 h / 20 °C
4.1: 34 percent / TFA / CH2Cl2 / 0.75 h / 20 °C
5.1: CH2Cl2 / HPLC on Chiracel OJ column separation
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

(S)-4-(2-aminoethoxy)-thalidomide

(S)-4-(2-aminoethoxy)-thalidomide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 97 percent / aq. HBr; AcOH / 2 h / 20 °C
2.1: dimethylformamide / 24 h / 60 °C
2.2: 71 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / dimethylformamide / 54 h / 63 °C
3.1: tetraethylammonium fluoride / 72 h / 20 °C
4.1: 34 percent / TFA / CH2Cl2 / 0.75 h / 20 °C
5.1: CH2Cl2 / HPLC on Chiracel OJ column separation
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

tert-butyl (2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)ethyl)carbamate
390367-45-0

tert-butyl (2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)ethyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 97 percent / aq. HBr; AcOH / 2 h / 20 °C
2.1: dimethylformamide / 24 h / 60 °C
2.2: 71 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / dimethylformamide / 54 h / 63 °C
3.1: tetraethylammonium fluoride / 72 h / 20 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

6-{6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-hexanoic acid {2-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yloxy]-ethyl}-amide

6-{6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-hexanoic acid {2-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yloxy]-ethyl}-amide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 97 percent / aq. HBr; AcOH / 2 h / 20 °C
2.1: dimethylformamide / 24 h / 60 °C
2.2: 71 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / dimethylformamide / 54 h / 63 °C
3.1: tetraethylammonium fluoride / 72 h / 20 °C
4.1: 34 percent / TFA / CH2Cl2 / 0.75 h / 20 °C
5.1: 70 percent / dimethylformamide / 3 h / 20 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

4-Hydroxythalidomide
5054-59-1

4-Hydroxythalidomide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 97 percent / aq. HBr; AcOH / 2 h / 20 °C
2.1: dimethylformamide / 24 h / 60 °C
2.2: 71 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / dimethylformamide / 54 h / 63 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

2-amino-N-(2,6-dioxo-piperidin-3-yl)benzamide

2-amino-N-(2,6-dioxo-piperidin-3-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / aq. HBr / acetic anhydride / 0.75 h / 50 °C
2: 39 percent / triethylamine / acetonitrile / 3 h / 60 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

2-azido-N-(2,6-dioxo-piperidin-3-yl)benzamide

2-azido-N-(2,6-dioxo-piperidin-3-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 96 percent / aq. HBr / acetic anhydride / 0.75 h / 50 °C
2.1: thionyl chloride / 2 h / 80 °C
2.2: 78 percent / triethylamine / dioxane / 40 - 50 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

2-benzyloxycarbonylamino-4-(4-oxo-3,4-dihydroquinazolin-2-yl)butyric acid

2-benzyloxycarbonylamino-4-(4-oxo-3,4-dihydroquinazolin-2-yl)butyric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: methyllithium / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
1.2: 52 percent / tetrahydrofuran / 20 °C
2.1: 38 percent / triethyl phosphite / toluene / 6 h / Heating
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione
55003-81-1

2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: AcOH / Heating
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

4-NT
19171-18-7

4-NT

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: AcOH / Heating
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

3-(7-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

3-(7-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: Et3N / dimethylformamide / 80 °C
3: H2 / 10 percent Pd/C / methanol
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

Lenalidomide
879126-98-4, 879126-99-5, 191732-72-6

Lenalidomide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: Et3N / dimethylformamide / 80 °C
3: H2 / 10 percent Pd/C / methanol
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / dimethyl sulfoxide
2: triethylamine / acetonitrile / 3 h / Reflux
3: 5%-palladium/activated carbon; hydrogen / ethanol / 1 h / 3040.2 Torr
View Scheme
Multi-step reaction with 3 steps
1: hydrogen bromide; acetic acid / 1 h / 60 °C
2: triethylamine / acetonitrile / 10 h / 20 - 80 °C
3: tin(ll) chloride / ethanol / 2 h / 15 - 80 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

3-(6-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

3-(6-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: Et3N / dimethylformamide / 80 °C
3: H2 / 10 percent Pd/C / methanol
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

3-(5-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

3-(5-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: Et3N / dimethylformamide / 80 °C
3: H2 / 10 percent Pd/C / methanol
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

3-(5-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

3-(5-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: Et3N / dimethylformamide / 80 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

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

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: Et3N / dimethylformamide / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogen bromide; acetic acid / 1 h / 60 °C
2: triethylamine / acetonitrile / 10 h / 20 - 80 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

3-(6-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
1063995-49-2

3-(6-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: Et3N / dimethylformamide / 80 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

2-(2,6-dioxo-3-piperidinyl)-5-amino-1H-isoindole-1,3(2H)-dione
191732-76-0

2-(2,6-dioxo-3-piperidinyl)-5-amino-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: AcOH / Heating
3: H2 / 10 percent Pd/C / acetone / 2585.74 - 3102.89 Torr
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

3-(4-nitro-3-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione
1063995-54-9

3-(4-nitro-3-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: Et3N / dimethylformamide / 80 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

pomalidomide
19171-19-8

pomalidomide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: AcOH / Heating
3: H2 / 10 percent Pd/C / acetone / 2585.74 - 3102.89 Torr
View Scheme

3-N-Cbz-amino-2,6-dioxopiperidine Chemical Properties

Molecule structure of 3-N-Cbz-amino-2,6-dioxopiperidine (CAS NO.24666-55-5):

Product Name: 3-N-Cbz-amino-2,6-dioxopiperidine
Molecular Formula: C13H14N2O4
Molecular Weight: 262.26 g/mol
CAS Registry Number: 24666-55-5 
Index of Refraction: 1.58
Molar Refractivity: 66.49 cm3
Molar Volume: 199.6 cm3
Polarizability: 26.36×10-24 cm3
Surface Tension: 55.5 dyne/cm
Density: 1.31 g/cm3
Flash Point: 268.4 °C
Enthalpy of Vaporization: 79.31 kJ/mol
Boiling Point: 520.2 °C at 760 mmHg
Vapour Pressure: 6.37E-11 mmHg at 25 °C 
SMILES: O=C2NC(=O)CCC2NC(=O)OCc1ccccc1
InChI: InChI=1/C13H14N2O4/c16-11-7-6-10(12(17)15-11)14-13(18)19-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,14,18)(H,15,16,17)
InChIKey: JJFWWAGUYKLJRN-UHFFFAOYAE
Std. InChI: InChI=1S/C13H14N2O4/c16-11-7-6-10(12(17)15-11)14-13(18)19-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,14,18)(H,15,16,17)
Std. InChIKey: JJFWWAGUYKLJRN-UHFFFAOYSA-N 
Product Categories of 3-N-Cbz-amino-2,6-dioxopiperidine (CAS NO.24666-55-5): N-CBZ

3-N-Cbz-amino-2,6-dioxopiperidine Specification

 3-N-Cbz-amino-2,6-dioxopiperidine (CAS NO.24666-55-5) is also named as Carbamic acid, (2,6-dioxo-3-piperidinyl)-, phenylmethyl ester (9CI) ;  REF DUPL: 3-N-Cbz-amino-2,6-Dioxo-piperidine ; Benzyl (2,6-dioxopiperidin-3-yl)carbamate .

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