1-N-CBZ-3-PIPERIDONE

1-N-CBZ-3-PIPERIDONE Property

Boiling point:

384.1±42.0 °C(Predicted)

Density 

1.212

storage temp. 

2-8°C

pka

-1.76±0.20(Predicted)

form 

Liquid

Appearance

Light yellow to yellow Liquid

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C13H15NO3/c15-12-7-4-8-14(9-12)13(16)17-10-11-5-2-1-3-6-11/h1-3,5-6H,4,7-10H2

InChIKey

ALXLNFWWLXCXSK-UHFFFAOYSA-N

SMILES

N1(C(OCC2=CC=CC=C2)=O)CCCC(=O)C1

CAS DataBase Reference

61995-20-8(CAS DataBase Reference)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

23-26-37-60

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

1-N-CBZ-3-PIPERIDONE Chemical Properties,Usage,Production

Uses

1-Benzyloxycarbonyl-3-piperidone finds its application in the synthesis and pharmacological evaluation of some 6-substituted 7-methyl-1,4-dioxa-7-azaspiro[4.5]decanes as potential dopamine agonists.

Synthesis

General procedure for the synthesis of 1-N-Cbz-3-piperidone from N-Benzyloxycarbonyl-3-hydroxypiperidine: N-Benzyloxycarbonyl-3-hydroxypiperidine (16.50 g, 70 mmol) was dissolved in dichloromethane (90 mL), stirred and cooled to 0 °C. Subsequently, N,N-diisopropylethylamine (DIPEA, 45.30 g, 0.35 mol) was added to the reaction system. A solution of dimethyl sulfoxide (DMSO, 100 mL) of pyridine trioxide (25.70 g, 0.16 mol) was slowly added dropwise at 0 °C. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 0°C for 2 hours. After completion of the reaction, the mixture was poured into 4 M hydrochloric acid and extracted with dichloromethane (100 mL x 3). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with the eluent ethyl acetate/petroleum ether (1/100 to 1/6, v/v) to afford 1-N-Cbz-3-piperidone (14.90 g, 90% yield) as an off-white solid. The structure of the product was confirmed by LC-MS, LC-MS: [M + H]+ = 234.

References

[1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 6, p. 1843 - 1845
[2] Patent: WO2014/32, 2014, A1. Location in patent: Page/Page column 45
[3] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 6, p. 811 - 814
[4] Patent: EP1757582, 2007, A1. Location in patent: Page/Page column 35-36
[5] Patent: WO2014/68527, 2014, A1. Location in patent: Page/Page column 75; 156; 157