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3-Hydroxypiperidine

3-Hydroxypiperidine structure

CAS No:
6859-99-0
Formula:
C5H11NO
Chemical Name:
3-Hydroxypiperidine
Synonyms:
3-Piperidinol;3-Piperidinol,(±)-;3-Hydroxypiperidine;3-Hydroxyhexahydropyridine;(±)-3-Hydroxypiperidine;(R,S)-3-Hydroxypiperidine;NSC 62082;41148-36-1
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

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Description

White to light yellow crystalline powder and lumps

3-Hydroxypiperidine Basic Attributes

Molecular Weight：

101.149

Exact Mass：

101.15

EC Number：

229-957-4

NSC Number：

62082

HScode：

2933399090

Characteristics

PSA：

32.3

XLogP3：

-0.3

Appearance：

White to light yellow crystalline powder and lumps

Density：

1.0±0.1 g/cm3

Melting Point：

60-63 °C

Boiling Point：

113-116 °C @ Press: 26 Torr

Flash Point：

104.5±13.3 °C

Refractive Index：

1.475

Water Solubility：

H2O: soluble

Storage Conditions：

2-8ºC

Safety Information

Packing level：

Ⅱ

Hazard category：

Transport codes：

3263

wgk germany：

hazard class code：

safety instructions：

S26-S36/37/39-S45

Marks：

C:Corrosive;

Precautionary statement(s)：

P280-P305 + P351 + P338-P310

Hazard Statements：

H314

GHS Classification：

|Danger|H314 (94%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 50 companies from 6 notifications to the ECHA C&L Inventory.

3-Hydroxypiperidine Use and Manufacturing

Methods of Manufacturing

In this embodiment, 3-hydroxypyridine is catalytically hydrogenated to prepare 3-hydroxy piperidine, and the specific method is as follows: 95 g of 3-hydroxypyridine (1.0 mol) and 600 mL of water were added to the high pressure reactor, After dissolving and stirring, 5.0 g of 5 wtpercent rhodium/silicon dioxide catalyst and 2.5 g of co-catalyst alumina were added. [0019] After three times of nitrogen substitution, hydrogen gas was introduced and the reaction was maintained at a pressure of 7 MPa and a temperature of 85° C until reaction was complete. [0020] After the reaction was completed, the mixture was filtered, the filtrate steamed off the water then subjected to distillation(6 5 ~ 6 7 °C, 2 mmHg) to give 3-hydroxypiperidine 99. 7g. The yield was 98.7percent and the GC content was 99.5percent.1g rhodium-nickel / carbon bimetallic catalyst (with rhodium content of 10percent, nickel content of 1percent), 3-hydroxy(0.11mol), phosphoric acid 0.3g (3.1mmol) and isopropanol (55mL) as the solvent. The reaction was carried out at 25oC for 3h. After hydrogenation, the catalyst was filtered off, The reaction mixture was concentrated under reduced pressure, and the resulting crude product was distilled under reduced pressure (65-67oC, 2 mmHg) to obtain 10.7 g of 3-hydroxypiperidine in 96percent yield;Compound 1 (110 kg), 5percent rhodium carbon (1 kg) and 100 L of water were charged in an autoclave under a hydrogen pressure of 6 MPa, 85 reaction conditions 5h. Cooled to room temperature, evacuated with hydrogen, and filtered to recover the rhodium carbon catalyst. The filtrate was reducedPressure to remove water, the residue continues to vacuum distillation, collecting 67-69 / 26.6Pa, after cooling solidified white solid 2(3-hydroxypiperidine) in a yield of 96.8percentN-benzyl-3-piperidinol (1.90 g, 9.93 mmol) was dissolved in THF: MeOH 1: 1, with 20percent Pd/C (0.5 g) and subjected to 50 psi of hydrogen gas for 16 hours. The crude product was then filtered through celite and then concentrated in vacuo. The crude product was determined to be pure (0.985 g, 98percent) BY LHNMR (400 MHz, CDC13) : 8 1.36 - 1. 56 (m, 2H), 1.68-1. 81 (m, 2H), 2.60-2. 76 (m, 3 H), 2.92 (dd, 1H, J=2.7, 11.9 Hz), 3.67 (sept, 1H, J=3.3 Hz).tert-Butyl 3-hydroxypiperidine-1-carboxya (1 g, 5 mmol) and HCl (2.0 M in EtOAc, 5 mL) were stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was neutralized by Sat. NaHCO

Uses

3-Hydroxypiperidine is usually used for Synthesis of unsymmetrical ureas,Synthesis of piperidine nucleoside analogs,Fluorination reactions,Synthesis of substituted pyridines.

Computed Properties

Molecular Weight:101.15
XLogP3:-0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:101.084063974
Monoisotopic Mass:101.084063974
Topological Polar Surface Area:32.3
Heavy Atom Count:7
Complexity:56
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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