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5382-16-1

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Basic Information
CAS No.: 5382-16-1
Name: 4-Hydroxypiperidine
Molecular Structure:
Molecular Structure of 5382-16-1 (4-Hydroxypiperidine)
Formula: C5H11NO
Molecular Weight: 101.15
Synonyms: Piperidin-4-ol;4-Piperidinol;3,4,5,6-tetrahydro-2H-pyridin-4-ol;4-Hydroxypiperidin;
EINECS: 226-373-1
Density: 1.016 g/cm3
Melting Point: 86-90 °C
Boiling Point: 222 °C at 760 mmHg
Flash Point: 107.8 °C
Solubility: soluble in water
Appearance: yellow to yellow-orange wet solid
Hazard Symbols: IrritantXi, CorrosiveC
Risk Codes: 36/37/38-34
Safety: 26-36-37/39-45-36/37/39-27
Transport Information: UN 3263
PSA: 32.26000
LogP: 0.05950
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Synthetic route
626-64-2

pyridin-4-ol

5382-16-1

4-HYDROXYPIPERIDINE

Conditions
ConditionsYield
In methanol; water100%
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

A

5382-16-1

4-HYDROXYPIPERIDINE

B

873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With phenol In acetonitrile Electrochemical reaction;A 100%
B n/a
109384-19-2

t-butyl 4-hydroxy piperidine-1-carboxylate

5382-16-1

4-HYDROXYPIPERIDINE

Conditions
ConditionsYield
With water at 100℃; for 10h;97%
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
65214-82-6

4-hydroxy-piperidine-1-carboxylic acid ethyl ester

5382-16-1

4-HYDROXYPIPERIDINE

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 130℃; for 3h; Heating;83%
6612-51-7

1-trimethylsilanyl-1,2,3,6-tetrahydro-pyridine

A

6859-99-0

3-hydroxypiperazine

B

5382-16-1

4-HYDROXYPIPERIDINE

Conditions
ConditionsYield
A 75%
B 25%
79508-92-2

1-allylpiperidin-4-ol

5382-16-1

4-HYDROXYPIPERIDINE

Conditions
ConditionsYield
Grubbs catalyst first generation In toluene for 4h; Heating;52%
383865-57-4

4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine

A

5382-16-1

4-HYDROXYPIPERIDINE

B

4-hydroxy-N-(4-methoxy-7-morpholin-4-yl-benzo[d]thiazol-2-yl)piperidine-1-carboxamide

Conditions
ConditionsYield
A n/a
B 50%
13169-00-1

Methoxyallene

79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

A

5382-16-1

4-HYDROXYPIPERIDINE

B

N-(tert-butoxycarbonyl)-4-[(Z)-3-methoxyprop-2-enyl]piperidin-4-ol

C

N-(tert-butoxycarbonyl)-4-[(E)-3-methoxyprop-2-enyl]piperidin-4-ol

Conditions
ConditionsYield
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
...Expand
13880-89-2

3-hydroxyglutaronitrile

5382-16-1

4-HYDROXYPIPERIDINE

Conditions
ConditionsYield
With ethanol; nickel at 50℃; under 36775.4 Torr; Hydrogenation;
13880-89-2

3-hydroxyglutaronitrile

A

5382-16-1

4-HYDROXYPIPERIDINE

B

38595-00-5

1,5-diamino-3-hydroxypentane

Conditions
ConditionsYield
With ethanol; nickel at 50℃; under 36775.4 Torr; Hydrogenation;
4-oxy-pyridine

4-oxy-pyridine

5382-16-1

4-HYDROXYPIPERIDINE

Conditions
ConditionsYield
With ethanol; sodium
With hydrogen; acetic acid; platinum
29976-53-2

N-ethoxycarbonyl-4-piperidone

5382-16-1

4-HYDROXYPIPERIDINE

Conditions
ConditionsYield
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

A

5382-16-1

4-HYDROXYPIPERIDINE

B

51462-38-5

N,N’-(2-chloroacetamidyl)-3,6-acridine

5382-16-1

4-HYDROXYPIPERIDINE

76-83-5

trityl chloride

227100-23-4

N-triphenylmethyl-4-hydroxypiperidine

Conditions
ConditionsYield
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
5382-16-1

4-HYDROXYPIPERIDINE

67852-85-1

glutaric acid chloride monobenzyl ester

N-(benzylglutaryl)-4-hydroxypiperidine

Conditions
ConditionsYield
In dichloromethane for 0.0833333h;100%
5382-16-1

4-HYDROXYPIPERIDINE

24424-99-5

di-tert-butyl dicarbonate

109384-19-2

t-butyl 4-hydroxy piperidine-1-carboxylate

Conditions
ConditionsYield
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%
5382-16-1

4-HYDROXYPIPERIDINE

109384-19-2

t-butyl 4-hydroxy piperidine-1-carboxylate

Conditions
ConditionsYield
With tert-butyldicarbonate; triethylamine In dichloromethane at 0℃; for 21h;100%
5382-16-1

4-HYDROXYPIPERIDINE

201338-62-7

N,N-tert-butoxycarbonyldehydroalanine

635712-79-7

(+/-)-2-(di-tert-butoxycarbonylamino)-3-(4-hydroxy-piperidin-1-yl)-propionic acid methyl ester

Conditions
ConditionsYield
In acetonitrile Nitrogen atmosphere;100%
5382-16-1

4-HYDROXYPIPERIDINE

16110-09-1

2,5 dichloropyridine

260441-44-9

2-(4-piperidinyloxy)-5-chloropyridine

Conditions
ConditionsYield
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
5382-16-1

4-HYDROXYPIPERIDINE

34619-03-9

tert-butyldicarbonate

109384-19-2

t-butyl 4-hydroxy piperidine-1-carboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane for 15h;100%
In tetrahydrofuran at 20℃;98.3%
With triethylamine In tetrahydrofuran at 20℃;98.3%
5382-16-1

4-HYDROXYPIPERIDINE

16182-04-0

Ethoxycarbonyl isothiocyanate

(4-hydroxypiperidine-1-carbothioyl)carbamic acid ethyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃;100%
5382-16-1

4-HYDROXYPIPERIDINE

67-64-1

acetone

5570-78-5

1-isopropylpiperidin-4-ol

Conditions
ConditionsYield
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;
5382-16-1

4-HYDROXYPIPERIDINE

4023-00-1

1H-Pyrazole-1-carboxamidine

887624-46-6

4-hydroxypiperidine-1-carboximidamide

Conditions
ConditionsYield
With triethylamine In acetonitrile at 60℃; for 12h;100%
5382-16-1

4-HYDROXYPIPERIDINE

1207547-20-3

(E)-1-((11-(1-cyanoethylidene)-6,11-dihydrodibenzo[b,e]oxepin-8-yl)methyl)-2-propyl-1H-benzo[d]imidazole-4-carboxylic acid

1207547-22-5

(E)-2-{8-[4-(4-hydroxy-1-piperidinecarbonyl)-2-propylbenzimidazol-1-yl]methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene}propiononitrile

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 15h;100%
5382-16-1

4-HYDROXYPIPERIDINE

57709-49-6

2-bromo-5-ethyl-[1,3,4]thiadiazole

1236284-56-2

1-(5-ethyl-1,3,4-thiadiazol-2-yl)piperidin-4-ol

Conditions
ConditionsYield
In ethanol at 140℃; for 1h; microwave reactor;100%
5382-16-1

4-HYDROXYPIPERIDINE

19064-67-6

6-chloro-2H-pyridazin-3-one

1542135-82-9

6-(4-hydroxypiperidin-1-yl)pyridazin-3(2H)-one

Conditions
ConditionsYield
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%
5382-16-1

4-HYDROXYPIPERIDINE

7461-50-9

2-chloropyrimidin-4-amine

2-(4-hydroxypiperidin-1-yl)pyrimidin-4-amine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 150℃; for 0.5h; Microwave irradiation;100%
5382-16-1

4-HYDROXYPIPERIDINE

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
ConditionsYield
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
5382-16-1

4-HYDROXYPIPERIDINE

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
ConditionsYield
With triethylamine In acetonitrile at 70 - 80℃;100%
5382-16-1

4-HYDROXYPIPERIDINE

(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
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;100%
5382-16-1

4-HYDROXYPIPERIDINE

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
ConditionsYield
In 1,4-dioxane for 10h; Reflux;100%
5382-16-1

4-HYDROXYPIPERIDINE

121-51-7

3-nitrobenzenesulphonyl chloride

873537-43-0

1-((3-nitrophenyl)sulfonyl)piperidin-4-ol

Conditions
ConditionsYield
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;
5382-16-1

4-HYDROXYPIPERIDINE

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
ConditionsYield
In N,N-dimethyl acetamide at 110℃; for 1h;100%
5382-16-1

4-HYDROXYPIPERIDINE

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
ConditionsYield
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%
5382-16-1

4-HYDROXYPIPERIDINE

36236-76-7

4-(bromomethyl)-2,2-dimethyl-1,3-dioxolane

64445-06-3

1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-4-piperidinol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 16h; Heating;99.8%
5382-16-1

4-HYDROXYPIPERIDINE

3-fluorophthalic acid diethyl ester

1234368-91-2

C17H23NO5

Conditions
ConditionsYield
In dimethyl sulfoxide at 80℃;99.4%
5382-16-1

4-HYDROXYPIPERIDINE

326818-08-0

4-[5-(Bromomethyl)-3-(4-fluoro-phenyl)-isoxazol-4-yl]-2-methanesulfonyl-pyrimidine

673451-66-6

C20H21FN4O4S

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 1.5h;99.2%
5382-16-1

4-HYDROXYPIPERIDINE

613-90-1

benzoyl cyanide

80213-01-0

(4-hydroxy-1-piperidinyl)(phenyl)methanone

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

The IUPAC name of 4-Hydroxypiperidine is piperidin-4-ol. With the CAS registry number 5382-16-1, it is also named as 4-Piperidinol; NSC 62083; AI3-39158. The product's categories are alcohols and derivatives, amines and anilines, piperidines, piperidones, piperazines, pyrans, piperidines & piperazines, piperidine, heterocyclic compounds and pyrans and piperidines & piperazines. It is yellow to yellow-orange wet solid which is soluble in water.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.61; (4)ACD/LogD (pH 7.4): -3.33; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.474; (13)Molar Refractivity: 27.99 cm3; (14)Molar Volume: 99.4 cm3; (15)Polarizability: 11.09×10-24 cm3; (16)Surface Tension: 33.7 dyne/cm; (17)Enthalpy of Vaporization: 53.31 kJ/mol; (18)Vapour Pressure: 0.0214 mmHg at 25°C; (19)Exact Mass: 101.084064; (20)MonoIsotopic Mass: 101.084064; (21)Topological Polar Surface Area: 32.3; (22)Heavy Atom Count: 7.

Uses of 4-Hydroxypiperidine: 1. It can react with 2-bromomethyl-[1,3]dioxolane to get 1-(1,3-dioxolan-2-ylmethyl)-4-piperidinol. This reaction needs reagent K2CO3 and solvent acetonitrile by heating. The reaction time is 15 hours. The yield is 83.5%.



2. It also reacts with 4-chloromethyl-[1,3]dioxolane to obtain 1-[1,3]dioxolan-4-ylmethyl-piperidin-4-ol. This reaction needs reagent K2CO3 and solvent acetonitrile by heating. The reaction time is 16 hours. The yield is 56.4%.

When you are using this chemical, please be cautious about it as the following:
It can causes burns. And it is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Take off immediately all contaminated clothing. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES: OC1CCNCC1;
2. InChI: InChI=1/C5H11NO/c7-5-1-3-6-4-2-5/h5-7H,1-4H2.