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675-20-7 Usage

Chemical Properties

white to yellowish low melting crystalline mass

Uses

δ-Valerolactam is a useful synthetic intermediate. It is an intermediate used to synthesize Cenicriviroc (C256550), an experimental drug candidate for the treatment of HIV infection. It is also a starting material for a new route to hexahydrojulolidines, using intramolecular 1,4-cycloaddition.

Definition

ChEBI: 2-Piperidone is a delta-lactam that is piperidine which is substituted by an oxo group at position 2. It has a role as an EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor. It is a member of piperidones and a delta-lactam.

Preparation

2-Piperidone can be obtained from cyclopentanone as raw material by a two-step reaction.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 7629, 1980 DOI: 10.1021/ja00546a001Tetrahedron Letters, 28, p. 2829, 1987 DOI: 10.1016/S0040-4039(00)96220-8The Journal of Organic Chemistry, 21, p. 965, 1956 DOI: 10.1021/jo01115a010

Purification Methods

Purify it by repeated fractional distillation.[Cowley J Org Chem 23 1330 1958, Reppe et al. Justus Liebigs Ann Chem 596 198 1955, IR: Huisgen et al. Chem Ber 90 1437 1957.] The hydrochloride has m 183-184o (from isoPrOH or EtOH/Et2O) [Hurd et al. J Org Chem 17 865 1952], and the oxime has m 122.5o (from pet ether) [Behringer & Meier Justus Liebigs Ann Chem 607 67 1957]. The picrate has m 92-93o. [Beilstein 21 H 239, 21 III/IV 3170, 21/6 V 396.]

Check Digit Verification of cas no

The CAS Registry Mumber 675-20-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,7 and 5 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 675-20:
(5*6)+(4*7)+(3*5)+(2*2)+(1*0)=77
77 % 10 = 7
So 675-20-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H9NO/c7-5-3-1-2-4-6-5/h1-4H2,(H,6,7)

675-20-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A12271)  delta-Valerolactam, 98%   

  • 675-20-7

  • 25g

  • 628.0CNY

  • Detail
  • Alfa Aesar

  • (A12271)  delta-Valerolactam, 98%   

  • 675-20-7

  • 100g

  • 2103.0CNY

  • Detail
  • Alfa Aesar

  • (A12271)  delta-Valerolactam, 98%   

  • 675-20-7

  • 500g

  • 6509.0CNY

  • Detail
  • Aldrich

  • (V209)  δ-Valerolactam  98%

  • 675-20-7

  • V209-25G

  • 694.98CNY

  • Detail
  • Aldrich

  • (V209)  δ-Valerolactam  98%

  • 675-20-7

  • V209-100G

  • 2,260.44CNY

  • Detail

675-20-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Piperidone

1.2 Other means of identification

Product number -
Other names 5-pentanelactam

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:675-20-7 SDS

675-20-7Synthetic route

2-hydroxypyridin
142-08-5

2-hydroxypyridin

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
Stage #1: 2-hydroxypyridin With palladium 10% on activated carbon; hydrogen; acetic acid at 24 - 28℃; for 15h;
Stage #2: In methanol
100%
With nickel-copper at 200 - 235℃; under 29420.3 Torr; Hydrogenation;
With 1,4-dioxane; palladium at 55℃; Hydrogenation;
With ethanol; nickel under 36775.4 - 73550.8 Torr; Hydrogenation;
With C33H49ClNRh; hydrogen In 2,2,2-trifluoroethanol; water at 70℃; under 7500.75 Torr; for 24h; Autoclave;99 %Chromat.
Cyclopentanone oxime
1192-28-5

Cyclopentanone oxime

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With aluminium trichloride at 40℃; for 0.5h; Rearrangement;100%
With tin(II) chloride dihdyrate; tetra-(n-butyl)ammonium iodide In acetonitrile for 0.5h; Beckmann Rearrangement; Molecular sieve; Reflux;96%
With silica gel; caesium carbonate; N-tosylimidazole In N,N-dimethyl-formamide for 2h; Beckmann rearrangement; Reflux;88%
5-aminopentanoic acid
660-88-8

5-aminopentanoic acid

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With silica gel In toluene for 1.5h; Heating;99%
With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 80℃; for 5h; Reagent/catalyst;99%
With 14C2H7N*14H(1+)*2H2O*2O(2-)*2Zr(4+)*O122P4W34(18-) In dimethyl sulfoxide at 70℃; for 24h;99%
C16H29NO3

C16H29NO3

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With acetic acid at 105℃; for 5h;98%
2-oxopiperidine-1-carboxylic acid tert-butyl ester
85908-96-9

2-oxopiperidine-1-carboxylic acid tert-butyl ester

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With water at 100℃; for 0.5h;97%
With silica gel; ytterbium(III) triflate In neat (no solvent) at 40℃; for 6h;96%
In acetonitrile at 300℃; under 75007.5 Torr;95%
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 50℃; for 18h; Sealed tube;94%
N-benzyloxycarbonyl-2-piperidone
106412-35-5

N-benzyloxycarbonyl-2-piperidone

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
Stage #1: N-benzyloxycarbonyl-2-piperidone With diethylaluminium chloride In hexane; dichloromethane at -78℃; for 0.166667h;
Stage #2: With methyl-phenyl-thioether In hexane; dichloromethane at 25℃; for 1h;
97%
N-cyclohexyl-2-thiazolinylsulfenamide
1089312-85-5

N-cyclohexyl-2-thiazolinylsulfenamide

5-aminopentanoic acid
660-88-8

5-aminopentanoic acid

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With triphenylphosphine96%
5-hydroxypentylamine
2508-29-4

5-hydroxypentylamine

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With Rh(trop2N)(PPh3); methacrylic acid methyl ester In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;96%
With dichloro(benzene)ruthenium(II) dimer; sodium hydride; acetonitrile; 1,3-di(propan-2-yl)-1H-imidazol-3-ium bromide In toluene for 36h; Inert atmosphere; Reflux;94%
With sodium hydride; dichloro(benzene)ruthenium(II) dimer; acetonitrile; 1,3-di(propan-2-yl)-1H-imidazol-3-ium bromide In toluene for 36h; Conversion of starting material; Inert atmosphere; Reflux;94%
cyclopentanone
120-92-3

cyclopentanone

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With sodium azide; sulfuric acid; silica gel at 60℃; for 0.416667h; Schmidt reaction;95%
With acetylhydroxamic acid; sulfuric acid In acetonitrile at 80℃; under 1292.9 Torr; for 0.133333h; Microwave irradiation;87%
With hydroxylamine hydrochloride at 120℃; for 6h; Beckmann rearrangement; neat (no solvent);80%
1-((R)-1-Phenyl-ethyl)-piperidin-2-one

1-((R)-1-Phenyl-ethyl)-piperidin-2-one

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With methanesulfonic acid In toluene for 6h; Heating;95%
5-hydroxypentylamine
2508-29-4

5-hydroxypentylamine

A

piperidine
110-89-4

piperidine

B

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With RuCl2[PPh2(CH2)4PPh2][2-(H2NCH2)C5H4N]; potassium hydroxide In toluene for 16h; Inert atmosphere; Reflux;A 7%
B 93%
With dodecacarbonyl-triangulo-triruthenium; N–phenyl–2–(dicyclohexylphosphino)pyrrole In cyclohexane at 140℃; for 21h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Autoclave;
δ-aminovaleric acid potassium salt

δ-aminovaleric acid potassium salt

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; bis(trichloromethyl) carbonate; potassium hydroxide In water; acetonitrile at 60℃; for 0.00277778h; Inert atmosphere;93%
2-Pyridone
142-08-5

2-Pyridone

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h;92%
N-benzyloxycarbonyl-5-aminovaleric acid succinimide ester
76944-94-0

N-benzyloxycarbonyl-5-aminovaleric acid succinimide ester

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate91%
5-azidopentanamide
1360453-32-2

5-azidopentanamide

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
Stage #1: 5-azidopentanamide With triphenylphosphine In tetrahydrofuran at 20℃; for 1h;
Stage #2: With water In tetrahydrofuran for 24h; Reflux;
91%
With tri-n-butyl-tin hydride In toluene for 24h; Reflux;84%
1-Azido-1-methylsulfanyl-cyclopentane

1-Azido-1-methylsulfanyl-cyclopentane

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform at 25℃; for 2h;88%
5-chloro-valeric acid
1119-46-6

5-chloro-valeric acid

A

piperidine
110-89-4

piperidine

B

piperidin-2-one
675-20-7

piperidin-2-one

C

1-pentanamine
110-58-7

1-pentanamine

D

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
Stage #1: 5-chloro-valeric acid With cyclopentyl methyl ether; ammonia at 200℃; under 4500.45 Torr; Sealed tube; Green chemistry;
Stage #2: With cyclopentyl methyl ether; ammonia; hydrogen at 200℃; under 42004.2 Torr; for 6.5h; Cooling with ice; Green chemistry;
A 85%
B 9%
C 2%
D 2%
piperidine
110-89-4

piperidine

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With 5.4 wt% Au/CeO2; water; oxygen In diethylene glycol dimethyl ether at 160℃; under 760.051 Torr; for 2.5h; Catalytic behavior; Schlenk technique;83%
With water; oxygen at 100℃; under 760.051 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Time; Green chemistry;80%
With oxygen; gold on silica dioxide In toluene at 100℃; for 100h;60%
Co{(N4C19H6(CH3)8)(CH2CH2COOC3H7)4(CH2COOC3H7)3}(CH2CHC(O)NHCH2CH2)(1+)

Co{(N4C19H6(CH3)8)(CH2CH2COOC3H7)4(CH2COOC3H7)3}(CH2CHC(O)NHCH2CH2)(1+)

A

3-methyl-2-pyrrolidinone
2555-05-7

3-methyl-2-pyrrolidinone

B

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
In methanol Irradiation (UV/VIS); anaerobic irradiation 1h with visible light at 20°C; analyzing products by GLC;A 83%
B 3%
In benzene Irradiation (UV/VIS); anaerobic irradiation 1h with visible light at 20°C; analyzing products by GLC;A 76%
B 2%
In water Irradiation (UV/VIS); anaerobic irradiation 1h with visible light in single-compartment vesicle of N,N-dihexadecyl-Nα-(6-(trimethylammonio)hexanoyl)-L-alaninamide bromide at 20°C; phosphate-borate buffer; analyzing products by GLC;A 63%
B 24%
3-phenylpropyl 4-cyanobutanoate

3-phenylpropyl 4-cyanobutanoate

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With platinum(IV) oxide; carbon monoxide; hydrogen In methanol at 25℃; for 72h; Autoclave; Inert atmosphere;80%
ethyl 5-azidovalerate
89896-39-9

ethyl 5-azidovalerate

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With water; triphenylphosphine In tetrahydrofuran for 12h; Ambient temperature;77%
cyclopentanone
120-92-3

cyclopentanone

A

piperidin-2-one
675-20-7

piperidin-2-one

B

Cyclopentanone oxime
1192-28-5

Cyclopentanone oxime

Conditions
ConditionsYield
With acetylhydroxamic acid; sulfuric acid In acetonitrile for 8h; Reflux;A 75%
B 6%
With ammonium hydroxide; molecular sieve; dihydrogen peroxide at 79.9℃; for 5h; other catalyst; further ketones;
4-cyanobutanoic acid ammonium salt

4-cyanobutanoic acid ammonium salt

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen; nickel In water at 70℃; under 25857.4 Torr; for 3.5h;74%
Cyclopentylmethylketoxim
90048-89-8

Cyclopentylmethylketoxim

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With sulfonated polymeric solid acid H-PDVB-SO3H In benzonitrile at 130℃; for 1h; Beckmann Rearrangement;74%
1-(trimethylsilyl)piperidin-2-one
3553-93-3

1-(trimethylsilyl)piperidin-2-one

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

A

piperidin-2-one
675-20-7

piperidin-2-one

B

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

C

2-(2-Oxo-piperidin-1-yl)-propionic acid ethyl ester

2-(2-Oxo-piperidin-1-yl)-propionic acid ethyl ester

D

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
at 155 - 180℃; for 3h; Yields of byproduct given;A n/a
B n/a
C 73%
D n/a
methyl (2S)-pyrrolidine carboxylate
2577-48-2

methyl (2S)-pyrrolidine carboxylate

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; Trimethylacetic acid In tetrahydrofuran at 0 - 20℃; for 0.166667h; Deamination;73%
((E)-1-Propenyl)-piperidin-2-one
642093-74-1

((E)-1-Propenyl)-piperidin-2-one

piperidin-2-one
675-20-7

piperidin-2-one

Conditions
ConditionsYield
Stage #1: ((E)-1-Propenyl)-piperidin-2-one With ruthenium trichloride; sodium periodate In water; 1,2-dichloro-ethane
Stage #2: With sodium hydrogencarbonate; sodium carbonate In water; 1,2-dichloro-ethane
70%
Multi-step reaction with 2 steps
1: NaIO4; aq. RuCl3 / 1,2-dichloro-ethane / 20 °C
2: 100 mg / aq. NaHCO3; Na2CO3 / acetone
View Scheme
methanol
67-56-1

methanol

N-chloro-δ-valerolactam
54468-04-1

N-chloro-δ-valerolactam

A

piperidin-2-one
675-20-7

piperidin-2-one

B

6-methoxypiperidin-2-one
63853-82-7

6-methoxypiperidin-2-one

Conditions
ConditionsYield
for 0.25h; Irradiation;A 5 % Chromat.
B 69%
piperidin-2-one
675-20-7

piperidin-2-one

1-nitrosopiperidin-2-one
50550-65-7

1-nitrosopiperidin-2-one

Conditions
ConditionsYield
With sodium acetate; dinitrogen tetraoxide In dichloromethane at -10℃; for 1h;100%
With 3,3-dimethyl-2-nitroso-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide In 1,2-dichloro-ethane at 80℃; Sealed tube;93%
With diethyl ether; nitrous anhydride unter Kuehlung;
piperidin-2-one
675-20-7

piperidin-2-one

chloral
75-87-6

chloral

1-(2,2,2-Trichloro-1-hydroxy-ethyl)-piperidin-2-one
65101-81-7

1-(2,2,2-Trichloro-1-hydroxy-ethyl)-piperidin-2-one

Conditions
ConditionsYield
In benzene for 2h; Heating;100%
piperidin-2-one
675-20-7

piperidin-2-one

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

N-(4-Methoxybenzyl)-δ-valerolactam
128773-73-9

N-(4-Methoxybenzyl)-δ-valerolactam

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Reflux; Inert atmosphere;100%
With sodium hydride In tetrahydrofuran for 23h; Heating;94%
With sodium t-butanolate In dimethyl sulfoxide at 20℃; for 3h;78%
With potassium hydroxide; tetrabutylammomium bromide In toluene for 8h; Heating;52%
With tetrabutylammomium bromide; potassium hydroxide In toluene for 8h; Dean-Stark;28.8 g
piperidin-2-one
675-20-7

piperidin-2-one

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-Benzenesulfonyl-3,4,5,6-tetrahydropyridin-2-one
7744-25-4

1-Benzenesulfonyl-3,4,5,6-tetrahydropyridin-2-one

Conditions
ConditionsYield
Stage #1: piperidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran; hexane at -78℃; for 4h; Inert atmosphere;
100%
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h;94%
With n-butyllithium 1.) THF, hexane, -60 deg C, 20 min, 2.) THF, hexane, from -60 deg C to 0 deg C, 2.5 h; Yield given. Multistep reaction;
piperidin-2-one
675-20-7

piperidin-2-one

ethyl acrylate
140-88-5

ethyl acrylate

1-(2-ethoxycarbonylethyl)-2-piperidinone
88948-40-7

1-(2-ethoxycarbonylethyl)-2-piperidinone

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran Michael addition reaction;100%
With tetraethoxy orthosilicate; cesium fluoride In neat (no solvent) at 25℃; for 0.166667h; Product distribution; Mechanism; variation of reaction time and amount of CsF; further α,β-unsaturated esters; further amides; presence of different solvents;98%
With tetraethoxy orthosilicate; cesium fluoride In neat (no solvent) at 25℃; for 0.166667h;98%
piperidin-2-one
675-20-7

piperidin-2-one

bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

1-t-Butoxycarbonylmethyl-2-piperidone
216252-69-6

1-t-Butoxycarbonylmethyl-2-piperidone

Conditions
ConditionsYield
Stage #1: piperidin-2-one With sodium hydride In toluene at 0℃; for 1h; Metallation;
Stage #2: bromoacetic acid tert-butyl ester at 20℃; for 10h; Alkylation;
100%
With P-tris(dimethylamino)-C-dimethylphosphonium ylide In tetrahydrofuran at -78 - 20℃; for 3h; Alkylation;71%
piperidin-2-one
675-20-7

piperidin-2-one

1-Bromo-2-butyne
3355-28-0

1-Bromo-2-butyne

1-but-2-ynyl-piperidin-2-one

1-but-2-ynyl-piperidin-2-one

Conditions
ConditionsYield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In tetrahydrofuran for 4h; Heating;100%
piperidin-2-one
675-20-7

piperidin-2-one

Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

4-(2-oxopiperidinomethyl)benzoate
1039889-84-3

4-(2-oxopiperidinomethyl)benzoate

Conditions
ConditionsYield
Stage #1: piperidin-2-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: Methyl 4-(bromomethyl)benzoate In N,N-dimethyl-formamide at 20℃; for 3h;
100%
piperidin-2-one
675-20-7

piperidin-2-one

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-oxopiperidine-1-carboxylic acid tert-butyl ester
85908-96-9

2-oxopiperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: piperidin-2-one With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at -78℃; for 0.5h; Further stages.;
99%
Stage #1: piperidin-2-one With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
98%
Stage #1: piperidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere;
97%
piperidin-2-one
675-20-7

piperidin-2-one

piperidine-2,6-dione
1121-89-7

piperidine-2,6-dione

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at 0 - 25℃; for 48h;99%
With manganese(II) triflate; 4,4'-diamino-2,2'-bipyridyl; dihydrogen peroxide In acetone at 20℃; for 1h; Reagent/catalyst;98%
With potassium peroxymonosulphate; water; potassium bromide In dichloromethane at 20℃; for 7h; Sealed tube; Irradiation;95%
With oxygen; titanium(IV) oxide In water for 48h; Irradiation;0.9 mmol
piperidin-2-one
675-20-7

piperidin-2-one

allyl bromide
106-95-6

allyl bromide

1-allyl-2-piperidinone
28737-46-4

1-allyl-2-piperidinone

Conditions
ConditionsYield
Stage #1: piperidin-2-one With sodium hydride In tetrahydrofuran
Stage #2: allyl bromide In tetrahydrofuran
99%
With sodium hydride In tetrahydrofuran at 20℃;92%
With potassium hydride In tetrahydrofuran at 0 - 20℃; for 20h;89%
piperidin-2-one
675-20-7

piperidin-2-one

Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

N-(4-ethoxycarbonylphenyl)-2-piperidone

N-(4-ethoxycarbonylphenyl)-2-piperidone

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 110℃; for 23h;99%
piperidin-2-one
675-20-7

piperidin-2-one

iodobenzene
591-50-4

iodobenzene

1-phenylpiperidin-2-one
4789-09-7

1-phenylpiperidin-2-one

Conditions
ConditionsYield
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In toluene at 110℃; for 8h;99%
With potassium phosphate; copper(l) iodide; N-Methyl-L-proline Methyl Ester In dimethyl sulfoxide at 110℃; for 5h; Goldberg reaction; Inert atmosphere;81%
With potassium carbonate In neat (no solvent) at 120℃; for 20h; Catalytic behavior; Green chemistry;75%
piperidin-2-one
675-20-7

piperidin-2-one

propargyl bromide
106-96-7

propargyl bromide

A

N-propargyl δ-valerolactam
18327-29-2

N-propargyl δ-valerolactam

B

N-(1,2-propadienyl)valerolactam
214219-69-9

N-(1,2-propadienyl)valerolactam

Conditions
ConditionsYield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In tetrahydrofuran for 4h; Heating;A n/a
B 99%
piperidin-2-one
675-20-7

piperidin-2-one

Benzyloxyacetyl chloride
19810-31-2

Benzyloxyacetyl chloride

1-(2-(benzyloxy)acetyl)piperidin-2-one
840-11-9

1-(2-(benzyloxy)acetyl)piperidin-2-one

Conditions
ConditionsYield
Stage #1: piperidin-2-one With pyridine; dmap In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: Benzyloxyacetyl chloride In dichloromethane at 50℃; for 16h; Inert atmosphere;
99%
With pyridine In toluene for 12h; Heating;2.95 g
piperidin-2-one
675-20-7

piperidin-2-one

3-chloro-4-fluorobenzyl bromide
192702-01-5

3-chloro-4-fluorobenzyl bromide

1-(3-chloro-4-fluorobenzyl)piperidin-2-one
865300-49-8

1-(3-chloro-4-fluorobenzyl)piperidin-2-one

Conditions
ConditionsYield
Stage #1: piperidin-2-one With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In tert-butyl methyl ether; water at 20 - 30℃; for 0.5h; Inert atmosphere; Large scale;
Stage #2: 3-chloro-4-fluorobenzyl bromide In tert-butyl methyl ether; water at 20 - 30℃; for 0.5h; Inert atmosphere; Large scale;
99%
Stage #1: piperidin-2-one With tert-butyl methyl ether; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 20 - 30℃; for 0.5h; Inert atmosphere; Large scale;
Stage #2: 3-chloro-4-fluorobenzyl bromide In water at 20 - 30℃; Inert atmosphere; Large scale;
99%
Stage #1: piperidin-2-one; tetrabutylammonium sulfate In tert-butyl methyl ether at 20℃; for 0.0833333h;
Stage #2: 3-chloro-4-fluorobenzyl bromide With sodium hydroxide In tert-butyl methyl ether; water at 20 - 30℃; for 4h;
Stage #1: piperidin-2-one With sodium hydride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0℃; for 0.583333h;
Stage #2: 3-chloro-4-fluorobenzyl bromide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0 - 20℃;
Stage #1: piperidin-2-one With sodium hydride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0℃; for 0.583333h;
Stage #2: 3-chloro-4-fluorobenzyl bromide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0 - 20℃;
piperidin-2-one
675-20-7

piperidin-2-one

4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline
929910-27-0

4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline

4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethyl-N-[piperidin-2-ylidene]aniline

4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethyl-N-[piperidin-2-ylidene]aniline

Conditions
ConditionsYield
Stage #1: piperidin-2-one With trichlorophosphate In toluene at 20℃; for 2h;
Stage #2: 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline In toluene for 5h; Heating / reflux;
Stage #3: With sodium hydroxide In water; toluene
99%
piperidin-2-one
675-20-7

piperidin-2-one

5-amino-valeric acid ; hydrochloride
627-95-2

5-amino-valeric acid ; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; water at 90℃; for 24h;98%
With water; hydrogen cation
piperidin-2-one
675-20-7

piperidin-2-one

(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

1-(3-phenylpropionyl)-2-piperidone
60437-57-2

1-(3-phenylpropionyl)-2-piperidone

Conditions
ConditionsYield
Stage #1: piperidin-2-one; (E)-3-phenylpropenal With Shvo's Catalyst In toluene at 100℃; for 24h; Inert atmosphere;
Stage #2: With hydrogen In toluene at 100℃; under 760.051 Torr; for 5h;
98%
piperidin-2-one
675-20-7

piperidin-2-one

C11H5BrF3N3S

C11H5BrF3N3S

2-(2-oxo-1-piperidinyl)-6-(4-trifluoromethylphenyl)imidazo[2,1-b]-[1,3,4]thiadiazole

2-(2-oxo-1-piperidinyl)-6-(4-trifluoromethylphenyl)imidazo[2,1-b]-[1,3,4]thiadiazole

Conditions
ConditionsYield
With potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃; for 0.25h; Buchwald-Hartwig Coupling; Inert atmosphere; Microwave irradiation;98%
piperidin-2-one
675-20-7

piperidin-2-one

benzyl chloride
100-44-7

benzyl chloride

ethyl iodide
75-03-6

ethyl iodide

3-ethyl-1-(phenylmethyl)-2-piperidinone
95936-18-8

3-ethyl-1-(phenylmethyl)-2-piperidinone

Conditions
ConditionsYield
Stage #1: piperidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere;
Stage #2: ethyl iodide In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;
Stage #3: benzyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Inert atmosphere;
98%
piperidin-2-one
675-20-7

piperidin-2-one

bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

1-(2-(benzyloxy)ethyl)piperidin-2-one
157399-43-4

1-(2-(benzyloxy)ethyl)piperidin-2-one

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) 0 deg C; 2.) heating;97%
piperidin-2-one
675-20-7

piperidin-2-one

benzyl bromide
100-39-0

benzyl bromide

N-benzyl-2-piperidinone
4783-65-7

N-benzyl-2-piperidinone

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78 - 20℃;97%
Stage #1: piperidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h;
Stage #2: benzyl bromide In tetrahydrofuran; hexane at -78 - 20℃;
97%
With n-butyllithium In tetrahydrofuran at -78 - 20℃;97%
piperidin-2-one
675-20-7

piperidin-2-one

2-(ethylthio)acetyl chloride
54256-37-0

2-(ethylthio)acetyl chloride

1-ethylsulfenylacetylpiperidin-2-one
221444-84-4

1-ethylsulfenylacetylpiperidin-2-one

Conditions
ConditionsYield
In benzene for 12h; Heating;97%
Heating;
In benzene

675-20-7Relevant articles and documents

PRODUCTION METHOD OF CYCLIC COMPOUND

-

Paragraph 0057; 0060; 0062; 0064, (2021/05/05)

PROBLEM TO BE SOLVED: To provide an industrially simple production method of a cyclic compound. SOLUTION: A production method of a cyclic compound includes a step to obtain a reduced form (B) by reducing an unsaturated bond in a ring structure of an aromatic compound (A) by means of catalytic hydrogenation of the aromatic compound (A) or its salt using palladium carbon as a catalyst under a normal pressure, in which the aromatic compound (A) has one or more ring structures selected from a group consisting of a five membered-ring, a six membered-ring, and a condensed ring of the five membered-ring or the six membered-ring with another six membered-ring, a hetero atom can be included in the ring structure, and the aromatic compound (A) can have one or two side chains bonded to the ring structure and does not have any carbon-carbon triple bond in the side chain. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

En Route to a Heterogeneous Catalytic Direct Peptide Bond Formation by Zr-Based Metal-Organic Framework Catalysts

Conic, Dragan,De Azambuja, Francisco,Harvey, Jeremy N.,Loosen, Alexandra,Parac-Vogt, Tatjana N.,Van Den Besselaar, Maxime

, p. 7647 - 7658 (2021/06/30)

Peptide bond formation is a challenging, environmentally and economically demanding transformation. Catalysis is key to circumvent current bottlenecks. To date, many homogeneous catalysts able to provide synthetically useful methods have been developed, while heterogeneous catalysts remain largely restricted to the studies addressing the prebiotic formation of peptides. Here, the catalytic activity of Zr6-based metal-organic frameworks (Zr-MOFs) toward peptide bond formation is investigated using dipeptide cyclization as a model reaction. Unlike previous catalysts, Zr-MOFs largely tolerate water, and reactions are carried out under ambient conditions. Notably, the catalyst is recyclable and no additives to activate the COOH group are necessary, which are common limitations of previous methods. In addition, a broad reaction scope tolerates substrates with bulky and Lewis basic groups. The reaction mechanism was assessed by detailed mechanistic and computational studies and features a Lewis acid activation of carboxylate groups by Zr centers toward amine addition in which an alkoxy ligand on adjacent Zr sites assists in lowering the barrier of key proton transfers. The proposed concepts were also used to study the formation of intermolecular peptide bond formation. While intrinsic challenges associated with the catalyst structure and water removal limit a more general intermolecular reaction scope under current conditions, the results suggest that further design of Zr-MOF catalysts could render these materials broadly useful as heterogeneous catalysts for this challenging transformation.

The benzyl can be selectively removed by visible light or near visible light. Method for protecting allyl and propargyl group

-

Paragraph 0010, (2021/10/16)

The invention provides a method for selectively removing benzyl, allyl and propargyl protecting groups by visible light or near visible light, namely a substrate containing benzyl, allyl or propargyl protecting groups. The method has the advantages of simple operation, safe and clean visible light or near visible light as excitation conditions, cheap and easily available reagents, high reaction yield, high reaction chemistry and regional selectivity, and is suitable for selective removal of benzyl, allyl and propargyl protecting groups in various substrates.

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