Nipecotic acid supplier | CasNO.498-95-3

Name
Nipecotic acid
EINECS 207-873-9
CAS No. 498-95-3
Article Data41
CAS DataBase
Density 1.125 g/cm³
Solubility Soluble in water
Melting Point 261 °C (dec.)(lit.)
Formula C₆H₁₁NO₂
Boiling Point 265.8 °C at 760 mmHg
Molecular Weight 129.159
Flash Point 114.5 °C
Transport Information
Appearance off-white to pale yellow-beige powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 3-Piperidinecarboxylicacid;Nipecoticacid (6CI,7CI,8CI);3-Carboxypiperidine;DL-Nipecotic acid;Hexahydronicotinic acid;3-Piperidinecarboxylic Acid;Piperidine-3-carboxylic acid;H-DL-Nip-OH;
PSA 49.33000
LogP 0.39940

Synthetic route

: 93-60-7
methyl 3-pyridinecarboxylate

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
With hydrogen In water at 120℃; under 11251.1 Torr; for 1h;	100%

: 59-67-6
nicotinic acid

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
With platinum(IV) oxide; hydrogen In ethanol at 80℃; under 6205.94 Torr; for 0.666667h; Microwave irradiation;	98%
With ethanol; sodium
With hydrogenchloride; platinum Hydrogenation;

: 141943-03-5
N-benzylnipecotic acid benzyl ester

A: 141943-04-6
1-benzylpiperidine-3-carboxylic acid

B: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
With cyclohexa-1,4-diene; hydrogen; palladium on activated charcoal In ethanol for 0.166667h; Ambient temperature;	A 63% B 30%

: 584-08-7
potassium carbonate

: 71962-74-8
Ethyl nipecotate

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
With Ki In ethyl acetate; acetone	55%

: 59-67-6
nicotinic acid

A: 498-95-3
nipecotic acid

B: 1,4,5,6-tetrahydronicotinate

Conditions

Conditions	Yield
With (S)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldicyclohexylphosphine; hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate In methanol at 60℃; under 75006 Torr; for 20h; Product distribution; Further Variations:; Reagents;	A 8% B n/a

: 110-89-4
piperidine

: 64-18-6
formic acid

A: 498-94-2
isonipecotic acid

B: 56-40-6
glycine

C: 4043-87-2
pipecolic Acid

D: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
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%

...Expand

: 89-00-9
Pyridine-2,3-dicarboxylic acid

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
With i-Amyl alcohol; sodium

: 50585-89-2
3-methoxycarbonylpiperidine

A: 1690-72-8
dihydroarecoline

B: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
at 150℃; under 0.01 Torr;

: 119228-39-6
Piperidine-3-carboxylic acid 4-nitro-phenyl ester

A: 100-02-7
4-nitro-phenol

B: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
With water at 37℃; pH 7.4; other nipecotic acid phenyl esters; various solutions;

: Piperidine-3-carboxylic acid 4-nitro-phenyl ester; hydrobromide

A: 100-02-7
4-nitro-phenol

B: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
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;

1.2.5.6-tetrahydro-pyridine-carboxylic acid-(3): 1.2.5.6-tetrahydro-pyridine-carboxylic acid-(3)

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
With acetic acid; platinum Hydrogenation;
With hydrogenchloride; platinum Hydrogenation;

: 7647-01-0
hydrogenchloride

: 498-96-4
guvacine

platinum black: platinum black

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 498-96-4
guvacine

: 64-19-7
acetic acid

platinum black: platinum black

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 59-67-6
nicotinic acid

: 64-17-5
ethanol

sodium: sodium

: 498-95-3
nipecotic acid

...Expand

: 89-00-9
Pyridine-2,3-dicarboxylic acid

: 123-51-3
i-Amyl alcohol

sodium: sodium

: 498-95-3
nipecotic acid

...Expand

: 7732-18-5
water

: 636-79-3
nicotinic acid hydrochloride

platinum oxide: platinum oxide

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
Hydration;

...Expand

: [(2-chloroethoxy)(3,4-chlorophenyl)(phenyl)]methane

: 71962-74-8
Ethyl nipecotate

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
Ki; potassium carbonate In N,N-dimethylformamide (DMF); chloroform
Ki; potassium carbonate In N,N-dimethylformamide (DMF); chloroform

: C15H36BrNO2Si3

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
With water; triethylamine In tetrahydrofuran; pentane at -60 - 20℃; for 4h;

: 4-(4-bromobutylidene)-2,2,6,6-tetramethyl-3,5-dioxa-2,6-disilaheptane

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / pentane / 2 h / 20 °C / Inert atmosphere 2: triethylamine; water / tetrahydrofuran; pentane / 4 h / -60 - 20 °C View Scheme

: 2067-33-6
5-bromopentanoic acid

: 498-95-3
nipecotic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / pentane / 2 h / 20 °C / Inert atmosphere 3: triethylamine; water / tetrahydrofuran; pentane / 4 h / -60 - 20 °C View Scheme

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

: 498-95-3
nipecotic acid

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

Conditions

Conditions	Yield
Stage #1: 2-chloro-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylnicotinonitrile; nipecotic acid With triethylamine In ethanol at 120℃; for 0.333333h; Microwave irradiation; Stage #2: With hydrogenchloride In water	100%

: 64-17-5
ethanol

: 498-95-3
nipecotic acid

: 4842-86-8
ethyl piperidine-3-carboxylate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 0℃; Reflux;	100%
With thionyl chloride at 0℃; for 24h; Reflux;	99%
With thionyl chloride In ethanol at -5℃; for 7h; Heating / reflux;	92%

: 5028-20-6
3-amino-2-methylaminopyridine

: 498-95-3
nipecotic acid

: C12H16N4

Conditions

Conditions	Yield
With polyphosphoric acid at 180℃; for 72h;	100%

: 452-58-4
2,3-Diaminopyridine

: 498-95-3
nipecotic acid

: C11H14N4

Conditions

Conditions	Yield
With polyphosphoric acid at 180℃; for 16h;	100%

: 67-56-1
methanol

: 498-95-3
nipecotic acid

: 89895-55-6
methyl piperidine-3-carboxylate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 3h;	98%
With thionyl chloride	97%
With thionyl chloride

: 501-53-1
benzyl chloroformate

: 498-95-3
nipecotic acid

: 78190-11-1
1-benzyloxycarbonylpiperidine-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane	98%
With sodium hydroxide In water at 20℃;	89%
With sodium hydroxide	82%

: 24424-99-5
di-tert-butyl dicarbonate

: 498-95-3
nipecotic acid

: 71381-75-4, 88495-54-9, 84358-12-3
N-(tert-butyloxycarbonyl)nipecotic acid

Conditions

Conditions	Yield
	98%
With sodium hydroxide In tert-butyl alcohol at 0 - 20℃; for 12h;	97%
With triethylamine In methanol at 0 - 20℃; Inert atmosphere;	97%

: 67-56-1
methanol

: 498-95-3
nipecotic acid

: 50585-89-2
3-methoxycarbonylpiperidine

Conditions

Conditions	Yield
With oxalyl dichloride at 0℃; for 1h;	98%
With sulfuric acid at 0 - 80℃;
With thionyl chloride at 0℃; for 1h; Inert atmosphere; Reflux;

: 29270-56-2
4-fluoro-7-nitro-2,1,3-benzoxadiazole

: 498-95-3
nipecotic acid

: rac-1-(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)piperidine-3-carboxylic acid

Conditions

Conditions	Yield
With sodium carbonate In water; acetonitrile at 0℃; for 0.116667h; Darkness;	98%

: 98-09-9
benzenesulfonyl chloride

: 498-95-3
nipecotic acid

: 321970-54-1
1-(phenylsulfonyl)piperidine-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: nipecotic acid With sodium carbonate In water at 0℃; for 0.166667h; Stage #2: benzenesulfonyl chloride In water at 0 - 20℃; Stage #3: With hydrogenchloride In water at 0 - 5℃; for 0.25 - 0.5h; pH=3;	97.83%
With sodium carbonate In dichloromethane; water at 25℃; for 16h; Inert atmosphere;	91%

: (E)-5,5-difluoro-7-(5-oxopentenyl)-1,3,10-trimethyl-5Hdipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-4-ium-5-uide

: 498-95-3
nipecotic acid

: rac-(E)-7-{5-[3-(carboxy)piperidin-1-yl]pentenyl}-5,5-difluor-1,3,10-trimethyl-5H-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-4-ium-5-uide

Conditions

Conditions	Yield
Stage #1: (E)-5,5-difluoro-7-(5-oxopentenyl)-1,3,10-trimethyl-5Hdipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-4-ium-5-uide; nipecotic acid With acetic acid In ethanol at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In ethanol at 20℃; Inert atmosphere;	96%

: 50-00-0
formaldehyd

: 485-72-3
7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on

: 498-95-3
nipecotic acid

: 1400917-40-9
1-{[7-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]methyl}piperidine-3-carboxylic acid

Conditions

Conditions	Yield
With dmap In ethanol Mannich Aminomethylation; Reflux; regioselective reaction;	95%

...Expand

: 98-88-4
benzoyl chloride

: 498-95-3
nipecotic acid

: 13850-76-5
(±)-1-benzoylpiperidine-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: benzoyl chloride; nipecotic acid With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 22h; Stage #2: With hydrogenchloride In water at 0℃; pH=1 - 2;	95%
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 22h;	95%
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 22h;	95%

: 78-39-7
Triethyl orthoacetate

: 498-95-3
nipecotic acid

: 2637-75-4
1-acetyl-piperidine-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In toluene at 110℃; for 24h;	94%

: 50-00-0
formaldehyd

: 24160-14-3
cladrin

: 498-95-3
nipecotic acid

: 1400917-43-2
1-{[7-hydroxy-3-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-8-yl]methyl}piperidine-3-carboxylic acid

Conditions

Conditions	Yield
With dmap In ethanol Mannich Aminomethylation; Reflux; regioselective reaction;	92%

...Expand

: 622-78-6
Benzyl isothiocyanate

: 498-95-3
nipecotic acid

: (±)-macahydantoins A

Conditions

Conditions	Yield
Stage #1: nipecotic acid With pyridine for 0.166667h; Stage #2: Benzyl isothiocyanate With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 65℃; for 8h; Inert atmosphere;	92%
Stage #1: Benzyl isothiocyanate; nipecotic acid With pyridine at 20℃; for 2h; Stage #2: With dmap; triethylamine; HATU at 20℃; for 6h; Reagent/catalyst; Cooling with ice; Inert atmosphere;	1.172 g

: 50-00-0
formaldehyd

: 128672-43-5
5-methylformononetin

: 498-95-3
nipecotic acid

: 1400917-38-5
1-{[7-hydroxy-3-(4-methoxyphenyl)-5-methyl-4-oxo-4H-chromen-8-yl]methyl}piperidine-3-carboxylic acid

Conditions

Conditions	Yield
With dmap In ethanol Mannich Aminomethylation; Reflux; regioselective reaction;	91%

...Expand

: 3392-12-9
Boc-Val-ONSu

: 498-95-3
nipecotic acid

: 208113-87-5
1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-piperidine-3-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 120℃; for 2.5h;	90%

: 98-59-9
p-toluenesulfonyl chloride

: 498-95-3
nipecotic acid

: 5134-62-3
1-tosylpiperidine-3-carboxylic acid

Conditions

Conditions	Yield
With sodium carbonate In water at 0 - 20℃; for 48h;	90%

: 14533-84-7
pentafluorophenyl trifloroacetate

: 498-95-3
nipecotic acid

: 1-(2,2,2-Trifluoro-acetyl)-piperidine-3-carboxylic acid pentafluorophenyl ester

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide Ambient temperature;	89%

: 498-95-3
nipecotic acid

: 112-67-4
n-hexadecanoyl chloride

: N-palmitoylpiperidine-3-carboxylic acid

Conditions

Conditions	Yield
With potassium carbonate In water; acetone at 0 - 20℃;	86%

: potassium phosphate

: 4-bromo-1-iodo-8,9-dihydro-7H-6-oxa-2,9a-diazabenzo[cd]azulene

: 498-95-3
nipecotic acid

: 1-(4-bromo-8,9-dihydro-7H-6-oxa-2,9a-diazabenzo[cd]azulen-1-yl)piperidine-3-carboxylic acid

Conditions

Conditions	Yield
With ammonia	86%

...Expand

: 1396776-39-8
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

: 498-95-3
nipecotic acid

: 1396771-96-2
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(1-(piperidine-3-carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Conditions

Conditions	Yield
Stage #1: N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide; nipecotic acid With triethylamine In dimethyl sulfoxide at 20℃; for 0.25h; Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide	85%

: 64-18-6
formic acid

: 498-95-3
nipecotic acid

: N-formylpiperidine-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: formic acid With acetic anhydride for 1h; Heating; Stage #2: nipecotic acid at 25℃; for 16h;	85%

: 498-95-3
nipecotic acid

: 74-88-4
methyl iodide

: 62581-21-9
3-carboxy-1,1-dimethyl-piperidinium; chloride

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 12h; Heating;	84%

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 498-95-3
nipecotic acid

: 71381-75-4, 88495-54-9, 84358-12-3
N-(tert-butyloxycarbonyl)nipecotic acid

Conditions

Conditions	Yield
With triethylamine In water; acetone	81%
With sodium hydrogencarbonate In 1,4-dioxane Acylation;
With triethylamine In water; acetone for 12h;

: 933674-72-7
2'-chlorobiphenyl-3-sulfonyl chloride

: 498-95-3
nipecotic acid

: 1394241-89-4
C18H18ClNO4S

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; acetone at 0 - 20℃; Inert atmosphere;	79%

: 1361955-58-9
methanesulfonic acid 2-methoxy-6-pentadecyl-benzyl ester

: 498-95-3
nipecotic acid

: 1363400-62-7
1-(2-methoxy-6-pentadecylbenzyl)piperidine-3-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 85℃;	76%

Nipecotic acid Chemical Properties

Molecular Structure of Nipecotic acid (CAS NO.498-95-3):

IUPAC Name: piperidine-3-carboxylic acid
Empirical Formula: C₆H₁₁NO₂
Molecular Weight: 129.157
Index of Refraction: 1.478
Surface Tension: 40.3 dyne/cm
Density: 1.125 g/cm³
Flash Point: 114.5 °C
Enthalpy of Vaporization: 55.45 kJ/mol
Boiling Point: 265.8 °C at 760 mmHg
Chemical Properties:off-white to pale yellow-beige powder
Vapour Pressure: 0.0026 mmHg at 25°C

Nipecotic acid Uses

Nipecotic acid is a GABA reuptake inhibitor.

Nipecotic acid Safety Profile

Hazard Codes Irritant Xi
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.

Nipecotic acid Specification

Nipecotic acid,its cas register number is 498-95-3. It also can be called (3R)-(-)-piperidin-3-ylcarboxylic acid;(+/-)-3-piperidine carboxylic acid ; 3-Piperidinecarboxylic acid ; L-nipecotic acid ; Dl-nipecotic acid ; Dl-3-piperidinecarboxylic acid ; (-)-D-nipecotic acid and so on.

Product Name

Nipecotic acid

Synthetic route

Nipecotic acid Chemical Properties

Nipecotic acid Uses

Nipecotic acid Safety Profile

Nipecotic acid Specification

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