1-Boc-4-(2-hydroxyethyl)piperidine Chemical Properties

Boiling point:

120-150 °C/0.5 mmHg (lit.)

Density 

1.043 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4730(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

viscous liquid

pka

15.10±0.10(Predicted)

color 

Colourless to light yellow

InChI

InChI=1S/C12H23NO3/c1-12(2,3)16-11(15)13-7-4-10(5-8-13)6-9-14/h10,14H,4-9H2,1-3H3

InChIKey

YBNJZIDYXCGAPX-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(CCO)CC1

CAS DataBase Reference

89151-44-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

HS Code 

2933399990

MSDS

• Language:English Provider:SigmaAldrich

1-Boc-4-(2-hydroxyethyl)piperidine Usage And Synthesis

Uses

N-BOC-4-piperidine-β-ethanol is used to prepare anilinoquinazoline VEGF receptor tyrosine kinase inhibitors with antitumor activities. It is also used to synthesize 1,3,4-trisubstituted pyrrolidine CCR5 receptor antagonists with antiviral activities.

Synthesis

General procedure for the synthesis of N-Boc-4-piperidine ethanol from tert-butyl 4-(2-ethoxy-2-oxo-substituted)piperidine-1-carboxylate: first, the above product (639 mg, 2.4 mmol) was dissolved in 6 mL of methanol, protected by argon, replaced three times with hydrogen and reacted overnight in a hydrogenation unit (4 atm H2). Upon completion of the reaction, the reaction solution was filtered through diatomaceous earth and washed with ethyl acetate. The filtrate was concentrated and purified by column chromatography to give a white solid product (722 mg, 100% yield). Subsequently, the above product (506 mg, 1.9 mmol) was dissolved in 10 mL of ether, cooled to -20 °C, and hydrogenated diisobutylaluminum (1.0 M, 5 mL, 5 mmol) was slowly added, and the reaction was carried out for 10 min until the raw material completely disappeared. The reaction mixture was poured into saturated potassium sodium tartrate solution and stirred at room temperature for 3 hours until clarified. The aqueous phase was extracted three times with ether, the organic phases were combined, washed with saturated NaCl solution and dried over anhydrous Na2SO4. After concentration, the product was purified by column chromatography to give a white solid product (368 mg, 86% yield).

References

[1] Patent: CN102952072, 2016, B. Location in patent: Paragraph 0110-0111
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
[3] Patent: US2012/71461, 2012, A1
[4] Patent: CN107793408, 2018, A
[5] Patent: WO2018/68297, 2018, A1

1-Boc-4-(2-hydroxyethyl)piperidine(89151-44-0)Related Product Information

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• Tris(trimethylsilyl)phosphate
• N-Methyldiethanolamine
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• Butyl acrylate