N-Boc-2-piperidone Chemical Properties

Melting point:

29-36 °C

Boiling point:

110°C/0.1mmHg(lit.)

Density 

1.099±0.06 g/cm3(Predicted)

Flash point:

>110 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Solid

pka

-2.29±0.20(Predicted)

color 

Off-White

BRN 

4674955

InChI

InChI=1S/C10H17NO3/c1-10(2,3)14-9(13)11-7-5-4-6-8(11)12/h4-7H2,1-3H3

InChIKey

ULMHMJAEGZPQRY-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCCCC1=O

CAS DataBase Reference

85908-96-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

N

Risk Statements 

50

Safety Statements 

24/25-61

RIDADR 

UN 3082

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29337900

MSDS

• Language:English Provider:ALFA

N-Boc-2-piperidone Usage And Synthesis

Chemical Properties

Off-White Low Melting Solid

Uses

N-Boc-2-piperidone(85908-96-9) is used as a synthetic intermediate in the preparation of various biological inhibitors.

Preparation

4-Benzensulfonylmethyl-4-hydroxy-piperidine TFA (B-1) Diisopropylethylamine (28.3 mL, 162.75 mmol) and di-t-butyl dicarbonate (28.4 g, 130.02 mmol) were added in sequence to a mixture of piperidone hydrate hydrochloride (12) (10.0 g, 65.1 mmol) in methanol (50 mL).  The mixture was stirred at room temperature for 20 hours. After that, removed the solvent  and the remaining was separated with ether and 1 M KHSO₄ solution.  The organic layer was washed with brine and saturated NaHCO₃.  Finally, N-Boc-2-piperidone was obtained after purification.

Definition

ChEBI:N-Boc-2-piperidone-protected by t-Boc. It is also known as 1-N-Boc-2-piperidone,1-N-Boc-2-piperidone, or 1-(tert-Butoxycarbonyl)-2-piperidone. 

Synthesis

To a solution of piperidin-2-one (0.97 g, 9.78 mmol) in dichloromethane (DCM, 20 mL) was sequentially added triethylamine (Et3N, 1.36 mL, 9.78 mmol), 4-dimethylaminopyridine (DMAP, 0.12 g, 0.978 mmol) and di-tert-butyl dicarbonate (Boc2O, 3.20 g, 14.7 mmol ). The reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography with the eluent ethyl acetate/petroleum ether (v/v = 1/7) to afford 1-Boc-2-piperidone as a light yellow oil (1.78 g, 91% yield). Mass spectrum (ESI, cation mode) m/z: 144.2 [(M-C4H8)+ H]+; 1H NMR (600 MHz, CDCl3): δ (ppm) 3.65 (t, J = 6.1 Hz, 2H), 2.50 (t, J = 9.6, 7.2 Hz, 2H), 1.82 (m, 4H), 1.52 (s, 9H).

References

[1] Journal of the American Chemical Society, 2008, vol. 130, # 23, p. 7449 - 7458
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
[3] Heterocycles, 2009, vol. 77, # 1, p. 417 - 432
[4] Patent: WO2015/94803, 2015, A1. Location in patent: Paragraph 395
[5] Patent: WO2016/190847, 2016, A1. Location in patent: Paragraph 0359

N-Boc-2-piperidone(85908-96-9)Related Product Information

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