5382-16-1

Basic information

• Product Name: 4-Hydroxypiperidine
• Synonyms: PIPERIDIN-4-OL;4-PIPERIDINOL;4PPOL;4-HYDROXYPIPERIDINE;HYDROXYPIPERIDINE(4-);AURORA KA-1006;4-Hydroxypiperidine base;4-Hydroxypiperidine/4-Piperidinol
• CAS NO: 5382-16-1
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.15
• EINECS: 226-373-1
• Product Categories: Alcohols and Derivatives;Amines and Anilines;Piperidines, Piperidones, Piperazines;Pyrans, Piperidines &Piperazines;Piperidine;Heterocyclic Compounds;NADIFLOXACIN;Pyrans, Piperidines & Piperazines;Building Blocks;C5 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines
• Mol File: 5382-16-1.mol
• Article Data: 36

Chemical Properties

• Melting Point: 86-90 °C
• Boiling Point: 108-114 °C10 mm Hg(lit.)
• Flash Point: 226 °F
• Appearance: yellow to yellow-orange wet solid
• Density: 0.9903 (rough estimate)
• Vapor Pressure: 0.0214mmHg at 25°C
• Refractive Index: 1.4400 (estimate)
• Storage Temp.: Room temperature.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.94±0.20(Predicted)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 102738
• CAS DataBase Reference: 4-Hydroxypiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxypiperidine(5382-16-1)
• EPA Substance Registry System: 4-Hydroxypiperidine(5382-16-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-36-37/39-45-36/37/39-27
• RIDADR: 3263
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5382-16-1(Hazardous Substances Data)

Usage

Chemical Properties

yellow to yellow-orange wet solid

Uses

Different sources of media describe the Uses of 5382-16-1 differently. You can refer to the following data:
1. 4-Hydroxypiperidine is used as a reagent for the synthesis of acridine (A190900) derivatives and fibrinogen receptor antagonists.
2. 4-Hydroxypiperidine (4-Piperidinol) can be used in the synthesis of a highly potent and selective IP (PGI(2) receptor) agonist. It can also be used in the study of copper-catalyzed N- versus O-arylation.

General Description

The molecular structure, vibrational spectra, NBO and UV-spectral analysis of 4-Hydroxypiperidine have been studied. The compounds with a substituted 4-piperidinol core have been found to be potent antagonists of the human H(3) receptor.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C5H11NO/c7-5-1-3-6-4-2-5/h5-7H,1-4H2/p+1

Synthetic route

pyridin-4-ol (626-64-2) → 4-HYDROXYPIPERIDINE (5382-16-1)

Conditions	Yield
In methanol; water	100%
With water; ruthenium Hydrogenation;
With water; pyrographite; ruthenium at 140℃; under 87525.4 Torr; Hydrogenation;
With hydrogenchloride; 5% active carbon-supported ruthenium; hydrogen In water at 95℃; under 26252.6 Torr; for 24h; Reagent/catalyst; Time; Autoclave;	99.5 %Chromat.

4-Hydroxy-piperidine-1-carboxylic acid (E)-3-phenyl-allyl ester → 4-HYDROXYPIPERIDINE (5382-16-1) + 1-propenylbenzene (873-66-5)

Conditions	Yield
With phenol In acetonitrile Electrochemical reaction;	A 100% B n/a

t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2) → 4-HYDROXYPIPERIDINE (5382-16-1)

Conditions	Yield
With water at 100℃; for 10h;	97%
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;

4-hydroxy-piperidine-1-carboxylic acid ethyl ester (65214-82-6) → 4-HYDROXYPIPERIDINE (5382-16-1)

Conditions	Yield
With potassium hydroxide In ethanol at 130℃; for 3h; Heating;	83%

1-trimethylsilanyl-1,2,3,6-tetrahydro-pyridine (6612-51-7) → 3-hydroxypiperazine (6859-99-0) + 4-HYDROXYPIPERIDINE (5382-16-1)

Conditions	Yield
	A 75% B 25%

1-allylpiperidin-4-ol (79508-92-2) → 4-HYDROXYPIPERIDINE (5382-16-1)

Conditions	Yield
Grubbs catalyst first generation In toluene for 4h; Heating;	52%

4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine (383865-57-4) → 4-HYDROXYPIPERIDINE (5382-16-1) + 4-hydroxy-N-(4-methoxy-7-morpholin-4-yl-benzo[d]thiazol-2-yl)piperidine-1-carboxamide

Conditions	Yield
	A n/a B 50%

Methoxyallene (13169-00-1) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4-HYDROXYPIPERIDINE (5382-16-1) + N-(tert-butoxycarbonyl)-4-[(Z)-3-methoxyprop-2-enyl]piperidin-4-ol + N-(tert-butoxycarbonyl)-4-[(E)-3-methoxyprop-2-enyl]piperidin-4-ol

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; tert-butyl alcohol In tetrahydrofuran at 20℃; for 16h; Title compound not separated from byproducts;	A 11% B n/a C n/a

3-hydroxyglutaronitrile (13880-89-2) → 4-HYDROXYPIPERIDINE (5382-16-1)

Conditions	Yield
With ethanol; nickel at 50℃; under 36775.4 Torr; Hydrogenation;

3-hydroxyglutaronitrile (13880-89-2) → 4-HYDROXYPIPERIDINE (5382-16-1) + 1,5-diamino-3-hydroxypentane (38595-00-5)

Conditions	Yield
With ethanol; nickel at 50℃; under 36775.4 Torr; Hydrogenation;

4-oxy-pyridine → 4-HYDROXYPIPERIDINE (5382-16-1)

Conditions	Yield
With ethanol; sodium
With hydrogen; acetic acid; platinum

N-ethoxycarbonyl-4-piperidone (29976-53-2) → 4-HYDROXYPIPERIDINE (5382-16-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: isobutyl bromide, Mg / diethyl ether / 10 h / Heating 2: 83 percent / KOH / ethanol / 3 h / 130 °C / Heating View Scheme

3,6-bis[(4'-hydroxypiperidino-acetyl)amino]-acridine hydrate → 4-HYDROXYPIPERIDINE (5382-16-1) + N,N’-(2-chloroacetamidyl)-3,6-acridine (51462-38-5)

4-HYDROXYPIPERIDINE (5382-16-1) + trityl chloride (76-83-5) → N-triphenylmethyl-4-hydroxypiperidine (227100-23-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%
With triethylamine In dichloromethane at 20℃; for 14h;	82%
With triethylamine In dichloromethane at 0℃; for 1h;
With potassium carbonate In N-methyl-acetamide

4-HYDROXYPIPERIDINE (5382-16-1) + glutaric acid chloride monobenzyl ester (67852-85-1) → N-(benzylglutaryl)-4-hydroxypiperidine

Conditions	Yield
In dichloromethane for 0.0833333h;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + di-tert-butyl dicarbonate (24424-99-5) → t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2)

Conditions	Yield
With sodium hydroxide In water; tert-butyl alcohol at 20℃;	100%
With sodium carbonate In dichloromethane; water for 72h;	100%
With sodium carbonate In dichloromethane; water for 72h; Inert atmosphere;	100%

4-HYDROXYPIPERIDINE (5382-16-1) → t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2)

Conditions	Yield
With tert-butyldicarbonate; triethylamine In dichloromethane at 0℃; for 21h;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + N,N-tert-butoxycarbonyldehydroalanine (201338-62-7) → (+/-)-2-(di-tert-butoxycarbonylamino)-3-(4-hydroxy-piperidin-1-yl)-propionic acid methyl ester (635712-79-7)

Conditions	Yield
In acetonitrile Nitrogen atmosphere;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + 2,5 dichloropyridine (16110-09-1) → 2-(4-piperidinyloxy)-5-chloropyridine (260441-44-9)

Conditions	Yield
Stage #1: 4-HYDROXYPIPERIDINE; 2,5 dichloropyridine With sodium hydride In 1,2-dimethoxyethane at 82℃; for 48h; Stage #2: With water In 1,2-dimethoxyethane	100%
With NaH In 1,2-dimethoxyethane; mineral oil

4-HYDROXYPIPERIDINE (5382-16-1) + tert-butyldicarbonate (34619-03-9) → t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane for 15h;	100%
In tetrahydrofuran at 20℃;	98.3%
With triethylamine In tetrahydrofuran at 20℃;	98.3%

4-HYDROXYPIPERIDINE (5382-16-1) + Ethoxycarbonyl isothiocyanate (16182-04-0) → (4-hydroxypiperidine-1-carbothioyl)carbamic acid ethyl ester

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + acetone (67-64-1) → 1-isopropylpiperidin-4-ol (5570-78-5)

Conditions	Yield
Stage #1: 4-HYDROXYPIPERIDINE; acetone With acetic acid In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20 - 40℃; for 2.75h; Stage #3: With ammonia In water for 0.5h; pH=9;	100%
Stage #1: 4-HYDROXYPIPERIDINE; acetone With acetic acid In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20 - 40℃; for 2.83333h; Stage #3: With ammonia; water for 0.5h; pH=9;	100%
Stage #1: 4-HYDROXYPIPERIDINE; acetone With acetic acid In 1,2-dichloro-ethane at 20℃; for 12h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 12h;	29%
Stage #1: 4-HYDROXYPIPERIDINE; acetone With sodium sulfate In chloroform at 20℃; for 24h; Stage #2: With sodium tris(acetoxy)borohydride In chloroform at 20℃; Stage #3: With methanol In chloroform at 20℃;
Stage #1: 4-HYDROXYPIPERIDINE; acetone In 1,2-dichloro-ethane at 20℃; for 1.5h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 18h;

4-HYDROXYPIPERIDINE (5382-16-1) + 1H-Pyrazole-1-carboxamidine (4023-00-1) → 4-hydroxypiperidine-1-carboximidamide (887624-46-6)

Conditions	Yield
With triethylamine In acetonitrile at 60℃; for 12h;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + (E)-1-((11-(1-cyanoethylidene)-6,11-dihydrodibenzo[b,e]oxepin-8-yl)methyl)-2-propyl-1H-benzo[d]imidazole-4-carboxylic acid (1207547-20-3) → (E)-2-{8-[4-(4-hydroxy-1-piperidinecarbonyl)-2-propylbenzimidazol-1-yl]methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene}propiononitrile (1207547-22-5)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 15h;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + 2-bromo-5-ethyl-[1,3,4]thiadiazole (57709-49-6) → 1-(5-ethyl-1,3,4-thiadiazol-2-yl)piperidin-4-ol (1236284-56-2)

Conditions	Yield
In ethanol at 140℃; for 1h; microwave reactor;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + 6-chloro-2H-pyridazin-3-one (19064-67-6) → 6-(4-hydroxypiperidin-1-yl)pyridazin-3(2H)-one (1542135-82-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 120℃; for 8h;	100%
With N-ethyl-N,N-diisopropylamine at 120℃; for 8h;	100%
In butan-1-ol at 140℃; for 214h;	67%

4-HYDROXYPIPERIDINE (5382-16-1) + 2-chloropyrimidin-4-amine (7461-50-9) → 2-(4-hydroxypiperidin-1-yl)pyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 150℃; for 0.5h; Microwave irradiation;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + bis(acetato-O)[(3S)-9,10-difluoro-2,3-dihydro-3-methyl-7-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylato-O6,O7]boron → bis(acetato-O)[(3S)-9-fluoro-10-(4-hydroxypiperidin-1-yl)-2,3-dihydro-3-methyl-7-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylato-O6,O7]boron

Conditions	Yield
With triethylamine In acetonitrile at 70 - 80℃;	100%
With triethylamine In water; acetonitrile at 65℃; for 3h;
With triethylamine In acetonitrile at 65℃; for 3.5h; Large scale;	10.7 kg

4-HYDROXYPIPERIDINE (5382-16-1) + bis(acetato-O)[(3R)-9,10-difluoro-3-(2-fluoromethyl)-2,3-dihydro-7-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylato-O6,O7]boron → C22H23BF2N2O9

Conditions	Yield
With triethylamine In acetonitrile at 70 - 80℃;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + (4,8-dibutyrylbenzo[1,2-d:4,5-d']bis[1,3]dioxol-2-yl)acetic acid → 1,1′-{2-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]benzo(1,2-d:4,5-d′)bis([1,3]dioxole)-4,8-diyl}bis(butan-1-one)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + 6-methyl-4-(methylthio)-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H )-one → 4-(4-hydroxypiperidin-1-yl)-6-methyl-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one

Conditions	Yield
In 1,4-dioxane for 10h; Reflux;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + 3-nitrobenzenesulphonyl chloride (121-51-7) → 1-((3-nitrophenyl)sulfonyl)piperidin-4-ol (873537-43-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	100%
Stage #1: 4-HYDROXYPIPERIDINE With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: 3-nitrobenzenesulphonyl chloride In dichloromethane at 20℃; for 1h;

4-HYDROXYPIPERIDINE (5382-16-1) + tert-butyl (3R)-3-[(6-chloro-5-fluoro-2-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-4-yl)oxy]piperidine-1-carboxylate → tert-butyl (3R)-3-{[5-fluoro-6-(4-hydroxypiperidin-1-yl)-2-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-4-yl]oxy}piperidine-1-carboxylate

Conditions	Yield
In N,N-dimethyl acetamide at 110℃; for 1h;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + 3-((2-chloro-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)amino)benzo[d]isothiazole-5-carbaldehyde → 1-((3-((2-chloro-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)amino)benzo[d]isothiazol-5-yl)methyl)piperidin-4-ol

Conditions	Yield
Stage #1: 4-HYDROXYPIPERIDINE; 3-((2-chloro-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)amino)benzo[d]isothiazole-5-carbaldehyde With acetic acid In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With sodium cyanoborohydride In N,N-dimethyl-formamide at 20℃; for 3h;	100%

4-HYDROXYPIPERIDINE (5382-16-1) + 4-(bromomethyl)-2,2-dimethyl-1,3-dioxolane (36236-76-7) → 1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-4-piperidinol (64445-06-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 16h; Heating;	99.8%

4-HYDROXYPIPERIDINE (5382-16-1) + 3-fluorophthalic acid diethyl ester → C17H23NO5 (1234368-91-2)

Conditions	Yield
In dimethyl sulfoxide at 80℃;	99.4%

4-HYDROXYPIPERIDINE (5382-16-1) + 4-[5-(Bromomethyl)-3-(4-fluoro-phenyl)-isoxazol-4-yl]-2-methanesulfonyl-pyrimidine (326818-08-0) → C20H21FN4O4S (673451-66-6)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 1.5h;	99.2%

4-HYDROXYPIPERIDINE (5382-16-1) + benzoyl cyanide (613-90-1) → (4-hydroxy-1-piperidinyl)(phenyl)methanone (80213-01-0)

Conditions	Yield
In dichloromethane at -10℃;	99%
In dichloromethane Ambient temperature;	95%

Upstream product

• 53821-46-8 Methyl 3-Methylquinoline-2-carboxylate 
• 53821-43-5 9-arabinofuranosyl-6-azidopurine 
• 53821-23-1 21-Docosenoic acid 
• 53821-20-8 ethyl-11-iodoundecanoate 
• 53821-16-2 Carbamic acid, (3-nitrophenyl)-, phenylmethyl ester (9CI) 
• 53821-12-8 Carbamic acid, (4-nitrophenyl)-, phenylmethyl ester (9CI) 
• 53821-11-7 2H-Benzimidazol-2-one,1,3-dihydro-1-hydroxy-(9CI) 
• 53821-06-0 N-(benzyloxy)-2-(4-methoxyphenyl)acetamide 
• 5382-10-5 1,2-(Methylenedioxy)-4-[2-(octylthio)propyl]benzene 
• 53820-86-3 1H-inden-1-yl 4-nitrobenzoate 
• 53820-85-2 1H-inden-3-yl 4-nitrobenzoate 
• 53820-70-5 (4S)-4a,5,6,7-Tetrahydro-4,6β-dihydroxy-3,4aβ,5β-trimethylnaphtho[2,3-b]furan-9(4H)-one 4,6-bis(2-methylpropenoate) 
• 53820-51-2 (4S)-4a,5,6,7-Tetrahydro-3,4aβ,5β-trimethyl-6β-hydroxy-4β-[(Z)-2-methyl-2-butenoyloxy]naphtho[2,3-b]furan-9(4H)-one 
• 53820-42-1 (E)-2-Methyl-2-butenoic acid (4S)-4,4a,5,6,7,8,8aβ,9-octahydro-5α-hydroxy-3,4aβ,5-trimethyl-9-oxonaphtho[2,3-b]furan-4β-yl ester 

Downstream Products

• 1116339-70-8 Ethyl 2-(4-hydroxypiperidin-1-yl)pyrimidine-5-carboxylate 
• 1116339-69-5 2-(4-Hydroxypiperidin-1-yl)pyrimidine-5-carboxylic acid 
• 54288-70-9 4-Bromopiperidine hydrobromide 
• 90729-43-4 Ebastine 
• 53179-11-6 Loperamide 
• 5570-77-4 4-Chloro-N-methylpiperidine 

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