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498-94-2

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498-94-2 Usage

Chemical Properties

white to faint pink-beige powder

Uses

A GABA-A receptor partial agonist

Synthesis Reference(s)

Synthesis, p. 623, 1984Tetrahedron Letters, 35, p. 8783, 1994 DOI: 10.1016/S0040-4039(00)78497-8

Purification Methods

It crystallises from H2O or EtOH as needles. The hydrochloride recrystallises from H2O or aqueous HCl with m 293odec (also 298odec, 300odec). [Wibaut Recl Trav Chim Pays-Bas 63 141 1944, IR: Zacharius et al. J Am Chem Soc 76 2908 1954, Beilstein 22/1 V 244.]

Check Digit Verification of cas no

The CAS Registry Mumber 498-94-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 8 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 498-94:
(5*4)+(4*9)+(3*8)+(2*9)+(1*4)=102
102 % 10 = 2
So 498-94-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H11NO2/c8-6(9)5-1-3-7-4-2-5/h5,7H,1-4H2,(H,8,9)

498-94-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (I0256)  4-Piperidinecarboxylic Acid  >98.0%(T)

  • 498-94-2

  • 25g

  • 380.00CNY

  • Detail
  • TCI America

  • (I0256)  4-Piperidinecarboxylic Acid  >98.0%(T)

  • 498-94-2

  • 100g

  • 990.00CNY

  • Detail
  • TCI America

  • (I0256)  4-Piperidinecarboxylic Acid  >98.0%(T)

  • 498-94-2

  • 500g

  • 3,690.00CNY

  • Detail
  • Alfa Aesar

  • (A11795)  Isonipecotic acid, 98%   

  • 498-94-2

  • 25g

  • 602.0CNY

  • Detail
  • Alfa Aesar

  • (A11795)  Isonipecotic acid, 98%   

  • 498-94-2

  • 100g

  • 1667.0CNY

  • Detail
  • Aldrich

  • (I18008)  Isonipecoticacid  97%

  • 498-94-2

  • I18008-25G

  • 547.56CNY

  • Detail
  • Aldrich

  • (I18008)  Isonipecoticacid  97%

  • 498-94-2

  • I18008-100G

  • 1,726.92CNY

  • Detail

498-94-2Synthetic route

Piperidine-4-carboxylic acid 3-methyl-but-2-enyl ester

Piperidine-4-carboxylic acid 3-methyl-but-2-enyl ester

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
With diethylamine; Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) In water; acetonitrile for 0.166667h; 5 molpercent catalyst;100%
Isonicotinic acid N-oxide
13602-12-5

Isonicotinic acid N-oxide

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
With ammonium formate; 10percent palladium on carbon In methanol at 20℃; for 16h;99%
benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate
10314-99-5

benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

A

isonipecotic acid
498-94-2

isonipecotic acid

B

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde
138163-08-3

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde

C

4-(4-Formyl-piperidine-1-carbonyl)-piperidine-1-carboxylic acid benzyl ester

4-(4-Formyl-piperidine-1-carbonyl)-piperidine-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
With methyl-phenyl-thioether; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal In toluene at 20℃; under 2068.6 Torr; for 22h; Yields of byproduct given;A n/a
B 94%
C n/a
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol for 2h;72%
piperidine
110-89-4

piperidine

formic acid
64-18-6

formic acid

A

isonipecotic acid
498-94-2

isonipecotic acid

B

glycine
56-40-6

glycine

C

pipecolic Acid
4043-87-2

pipecolic Acid

D

nipecotic acid
498-95-3

nipecotic acid

Conditions
ConditionsYield
In water at 10 - 20℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA);A 4.3%
B 0.1%
C 0.8%
D 2.9%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
With i-Amyl alcohol; sodium
With acetic acid; platinum at 40℃; under 2280 Torr; Hydrogenation;
With acetic acid; platinum Hydrogenation;
4-bromo-2-(2-bromo-ethyl)-butyric acid ethyl ester
857778-39-3

4-bromo-2-(2-bromo-ethyl)-butyric acid ethyl ester

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
With ammonia at 130 - 140℃;
2,6-dichloropyridine-4-carboxylic acid
5398-44-7

2,6-dichloropyridine-4-carboxylic acid

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
With acetic acid; platinum Hydrogenation;
Multi-step reaction with 2 steps
1: Raney nickel; aqueous NaOH / Hydrogenation.unter Druck
2: platinum; acetic acid / Hydrogenation
View Scheme
Conditions
ConditionsYield
With perchloric acid; ammonium sulfamate; sodium thiocyanide at 50℃; Rate constant; piperidinium perchlorate, 18h; transnitrosating studies;
Piperidine-4-carboxylic acid 4-nitro-phenyl ester; hydrobromide

Piperidine-4-carboxylic acid 4-nitro-phenyl ester; hydrobromide

A

isonipecotic acid
498-94-2

isonipecotic acid

B

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With Cu complex of polymer from 2,6-bis-aminomethylpyridine and 4,4'-bis-aminomethyldiphenylmethane; water In dimethyl sulfoxide at 25℃; Rate constant; var.reag.: Cu(2+) complex of 2,6-bis-benzylaminomethylpyridine; oligomers of 2,6-bis-aminomethylpyridine and 4,4'-bis-aminomethyldiphenylmethane;
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

acetic acid
64-19-7

acetic acid

platinum

platinum

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
Hydrogenation;
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

pentan-1-ol
71-41-0

pentan-1-ol

sodium

sodium

isonipecotic acid
498-94-2

isonipecotic acid

1-benzyloxycarbonylpiperidine-4-carboxylic acid
10314-98-4

1-benzyloxycarbonylpiperidine-4-carboxylic acid

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C
2: H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr
View Scheme
Piperidine-1,4-dicarboxylic acid 1-allyl ester 4-(3-methyl-but-2-enyl) ester

Piperidine-1,4-dicarboxylic acid 1-allyl ester 4-(3-methyl-but-2-enyl) ester

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / diethylamine / Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) / acetonitrile; H2O / 0.33 h / 1 molpercent catalyst
2: 100 percent / diethylamine / Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) / acetonitrile; H2O / 0.17 h / 5 molpercent catalyst
View Scheme

A

B

1-(dimethylcarbamoyl)piperidine-4-carboxylic acid

1-(dimethylcarbamoyl)piperidine-4-carboxylic acid

C

tetramethylurea
632-22-4

tetramethylurea

4-carboxamidopiperidine
39546-32-2

4-carboxamidopiperidine

isonipecotic acid
498-94-2

isonipecotic acid

Conditions
ConditionsYield
With amidase from Cupriavidus necator JMP134; water In aq. phosphate buffer at 30℃; pH=7; Enzymatic reaction; stereoselective reaction;
isonipecotic acid
498-94-2

isonipecotic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

1-benzyloxycarbonylpiperidine-4-carboxylic acid
10314-98-4

1-benzyloxycarbonylpiperidine-4-carboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium carbonate In water; acetonitrile at 0 - 20℃; for 2h; pH=10 - 11;100%
With potassium carbonate In water at 22℃; for 58h;97%
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃;96%
isonipecotic acid
498-94-2

isonipecotic acid

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-(4-piperidinyl)-1H-benzimidazole
38385-95-4

2-(4-piperidinyl)-1H-benzimidazole

Conditions
ConditionsYield
Stage #1: isonipecotic acid; 1,2-diamino-benzene at 190℃; for 14h;
Stage #2: isonipecotic acid; 1,2-diamino-benzene With phosphoric acid
100%
With PPA at 100℃; for 2h;92%
With PPA at 180℃; for 2h;85%
isonipecotic acid
498-94-2

isonipecotic acid

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid
84358-13-4

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

Conditions
ConditionsYield
In dichloromethane100%
In sodium hydroxide; tert-butyl alcohol100%
In sodium hydroxide; tert-butyl alcohol100%
isonipecotic acid
498-94-2

isonipecotic acid

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

1-[1-(diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid
874800-95-0

1-[1-(diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid

Conditions
ConditionsYield
With methanol; polymer-bound trimethyl ammonium cyanoborohydride; acetic acid at 120℃; for 0.0833333h; Polystyrene; Microwave irradiation;100%
isonipecotic acid
498-94-2

isonipecotic acid

phenyl chloroformate
1885-14-9

phenyl chloroformate

1-benzyloxycarbonylpiperidine-4-carboxylic acid
10314-98-4

1-benzyloxycarbonylpiperidine-4-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 25℃; for 18h;100%
isonipecotic acid
498-94-2

isonipecotic acid

1-[3-chloro-5-(5-ethyl-1,2,4-oxadiazol-3-yl)pyridin-2-yl]piperazine bis(trifluoroacetate)

1-[3-chloro-5-(5-ethyl-1,2,4-oxadiazol-3-yl)pyridin-2-yl]piperazine bis(trifluoroacetate)

1-(3-cyano-5-(isopropoxycarbonyl)-6-methylpyridin-2-yl)piperidine-4-carboxylic acid
898227-66-2

1-(3-cyano-5-(isopropoxycarbonyl)-6-methylpyridin-2-yl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: isonipecotic acid; 1-[3-chloro-5-(5-ethyl-1,2,4-oxadiazol-3-yl)pyridin-2-yl]piperazine bis(trifluoroacetate) With N-ethyl-N,N-diisopropylamine In ethanol for 1h; Heating / reflux;
Stage #2: With potassium hydrogensulfate In ethanol; water at 20℃;
100%
isonipecotic acid
498-94-2

isonipecotic acid

2-chloro-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylnicotinonitrile
898229-16-8

2-chloro-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylnicotinonitrile

1-[3-cyano-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylpyridin-2-yl]piperidine-4-carboxylic acid
898229-21-5

1-[3-cyano-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylpyridin-2-yl]piperidine-4-carboxylic acid

Conditions
ConditionsYield
at 120℃; for 0.666667h; Microwave irradiation;100%
isonipecotic acid
498-94-2

isonipecotic acid

isopropyl 6-chloro-3-cyano-2-methylnicotinate
898227-65-1

isopropyl 6-chloro-3-cyano-2-methylnicotinate

1-(3-cyano-5-(isopropoxycarbonyl)-6-methylpyridin-2-yl)piperidine-4-carboxylic acid
898227-66-2

1-(3-cyano-5-(isopropoxycarbonyl)-6-methylpyridin-2-yl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: isonipecotic acid; isopropyl 6-chloro-3-cyano-2-methylnicotinate With N-ethyl-N,N-diisopropylamine In ethanol for 1h; Heating / reflux;
Stage #2: With potassium hydrogensulfate In ethanol; water at 20℃;
100%
Stage #1: isonipecotic acid; isopropyl 6-chloro-3-cyano-2-methylnicotinate With N-ethyl-N,N-diisopropylamine In ethanol for 1h; Heating / reflux;
Stage #2: With potassium hydrogensulfate In ethanol; water
100%
isonipecotic acid
498-94-2

isonipecotic acid

1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

methylamine
74-89-5

methylamine

1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylicacid
1141894-74-7

1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylicacid

Conditions
ConditionsYield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; methylamine With sodium hydroxide In water; acetonitrile at 0℃; for 0.5h; pH=9 - 10;
Stage #2: isonipecotic acid In water; acetonitrile at 0 - 20℃; for 1h; pH=9 - 10;
100%
isonipecotic acid
498-94-2

isonipecotic acid

4-(chloromethyl)-2-(4-fluorophenyl)-5-methyl-1,3-oxazole
625826-69-9

4-(chloromethyl)-2-(4-fluorophenyl)-5-methyl-1,3-oxazole

1-((2-(4-fluorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

1-((2-(4-fluorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 16h;100%
isonipecotic acid
498-94-2

isonipecotic acid

4-(chloromethyl)-5-methyl-2-(2,6-difluorophenyl)oxazole

4-(chloromethyl)-5-methyl-2-(2,6-difluorophenyl)oxazole

1-((2-(2,6-difluorolphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

1-((2-(2,6-difluorolphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 16h;100%
isonipecotic acid
498-94-2

isonipecotic acid

4-(chloromethyl)-5-methyl-2-(2,6-dibromophenyl)oxazole

4-(chloromethyl)-5-methyl-2-(2,6-dibromophenyl)oxazole

1-((2-(2,6-dibromophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

1-((2-(2,6-dibromophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 16h;100%
isonipecotic acid
498-94-2

isonipecotic acid

4-(chloromethyl)-5-methyl-2-(2-fluoro-6-methylphenyl)oxazole

4-(chloromethyl)-5-methyl-2-(2-fluoro-6-methylphenyl)oxazole

1-((2-(2-fluoro-6-methylphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

1-((2-(2-fluoro-6-methylphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 16h;100%
isonipecotic acid
498-94-2

isonipecotic acid

4-(chloromethyl)-5-methyl-2-(2-methoxy-6-methylphenyl)oxazole

4-(chloromethyl)-5-methyl-2-(2-methoxy-6-methylphenyl)oxazole

1-((2-(2-methoxy-6-methylphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

1-((2-(2-methoxy-6-methylphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 16h;100%
isonipecotic acid
498-94-2

isonipecotic acid

4-(5-chlorosulfonyl-2-n-propoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide
374776-34-8

4-(5-chlorosulfonyl-2-n-propoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

4-(5-(4-(hydroxycarbonyl)piperidinylsulfonyl)-2-n-propoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

4-(5-(4-(hydroxycarbonyl)piperidinylsulfonyl)-2-n-propoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 2h;99%
isonipecotic acid
498-94-2

isonipecotic acid

ethanol
64-17-5

ethanol

piperidine-4-carboxylic acid ethyl ester hydrochloride

piperidine-4-carboxylic acid ethyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride for 3.83333h; Cooling with ice; Reflux;99%
With thionyl chloride at 0℃; for 3h; Reflux;96%
Stage #1: isonipecotic acid; ethanol With thionyl chloride at 0℃; for 3h; Heating / reflux;
Stage #2: With hydrogenchloride In ethanol
90.2%
With thionyl chloride at 0 - 90℃; for 6h;80.05%
With thionyl chloride Inert atmosphere; Reflux;
isonipecotic acid
498-94-2

isonipecotic acid

copper(II) perchlorate hexahydrate

copper(II) perchlorate hexahydrate

[Cu(piperidine-4-carboxylic acid)4][ClO4]2

[Cu(piperidine-4-carboxylic acid)4][ClO4]2

Conditions
ConditionsYield
In water soln. of metal compd. added to aq. soln. of ligand (1:4), stirred at 70°C for 10 min; crystd. on storage for several h, elem. anal.;99%
isonipecotic acid
498-94-2

isonipecotic acid

4-(chloromethyl)-5-methyl-2-(2,6-dichlorophenyl)oxazole

4-(chloromethyl)-5-methyl-2-(2,6-dichlorophenyl)oxazole

1-((2-(2,6-dichlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

1-((2-(2,6-dichlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 16h;99%
isonipecotic acid
498-94-2

isonipecotic acid

4-(chloromethyl)-5-methyl-2-(2-fluoro-6-methoxyphenyl)oxazole

4-(chloromethyl)-5-methyl-2-(2-fluoro-6-methoxyphenyl)oxazole

1-((2-(2-fluoro-6-methoxyphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

1-((2-(2-fluoro-6-methoxyphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 16h;99%

498-94-2Relevant articles and documents

Electrocatalytic synthesis of isonipecotic acid

Osadchenko,Tomilov

, p. 499 - 500 (2006)

An electrocatalytic synthesis of isonipecotic acid was carried out by cathodic reduction of isonicotinic acid in a membrane electrolyzer on a copper cathode activated with Raney nickel in an alkaline medium under mild conditions. Pleiades Publishing, Inc., 2006.

High-efficiency synthesis method of methyl 4-piperidineacetate

-

Paragraph 0030; 0040; 0046; 0050; 0051; 0060; 0070, (2019/01/14)

The invention discloses a high-efficiency synthesis method of methyl 4-piperidineacetate. The high-efficiency synthesis method comprises the following steps: firstly, preparing a colloid; secondly, taking titanium tetrachloride, di-n-octyl ether, cetylamine and carbon disulfide as raw materials to prepare reaction liquid; adding the reaction liquid into the colloid and dropwise adding ammonia water for precipitating to prepare a catalyst; taking 4-picolinic acid as a raw material and preparing 4-nipecotic acid under the reaction of the catalyst; taking the 4-nipecotic acid as the raw materialto prepare the methyl 4-piperidineacetate. The method has the advantages of simple operation, low preparation cost, high yield of a target product and easiness in separation.

Use of Functionalized Onium Salts for Peptide Synthesis

-

, (2010/12/18)

A subject of the invention is the use of a salt with a dedicated task of formula (I): [in-line-formulae]A+-L-R—OY, X?[/in-line-formulae] as soluble support for peptide synthesis, in which: X? represents a functional or non-functional anion,Y represents either a hydrogen atom, or a —COOR1 group, R1 representing in particular an alkyl group comprising 1 to 20 carbon atoms,A+ represents a cationic entity,L represents an arm, in particular an alkyl group of 3 to 20 carbon atoms,R represents in particular a group of formula —C(Ra)(Rb)—, Ra and Rb representing independently of one another in particular a hydrogen or an alkyl group, comprising 1 to 20 carbon atoms.

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