1,4-Oxazepan-5-one

1,4-Oxazepan-5-one Property

Melting point:

80-82°C

Boiling point:

165 °C(Press: 15 Torr)

Density 

1.068±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

15.85±0.20(Predicted)

Appearance

Off-white to yellow Solid

Sensitive 

Hygroscopic

InChI

InChI=1S/C5H9NO2/c7-5-1-3-8-4-2-6-5/h1-4H2,(H,6,7)

InChIKey

OXDIYMHNQAWSCL-UHFFFAOYSA-N

SMILES

O1CCC(=O)NCC1

Safety

PackingGroup 

III

HS Code 

2934999090

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.

1,4-Oxazepan-5-one Chemical Properties,Usage,Production

Uses

Used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 1,4-oxoazepan-5-one from dihydro-2H-pyran-4(3H)-one oxime: to a solution of tetrahydrofuran (THF, 10 mL) containing the ketoxime (0.01 mol) was added T3P (15 mol%, 50% solution in ethyl acetate). The reaction mixture was heated to reflux and stirred for 1-4 h under nitrogen protection. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the solvent was removed under reduced pressure. The residue was diluted with distilled water (20 mL) and subsequently extracted with ethyl acetate (2 x 20 mL). The organic phases were combined and washed sequentially with saturated sodium bicarbonate (NaHCO3) solution (1 × 10 mL) and brine. The organic phase was dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give a high purity target amide product.

References

[1] Tetrahedron Letters, 2011, vol. 52, # 10, p. 1074 - 1077
[2] Patent: WO2012/101654, 2012, A2. Location in patent: Page/Page column 67-68
[3] Zhurnal Obshchei Khimii, 1955, vol. 25, p. 133,135; engl. Ausg. S. 119, 121
[4] Zhurnal Obshchei Khimii, 1955, vol. 25, p. 133,135; engl. Ausg. S. 119, 121
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2651 - 2653