1-(METHYLSULFONYL)PIPERIDIN-4-AMINE

1-(METHYLSULFONYL)PIPERIDIN-4-AMINE Property

Boiling point:

296.0±50.0 °C(Predicted)

Density 

1.27±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

9.45±0.20(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C6H14N2O2S/c1-11(9,10)8-4-2-6(7)3-5-8/h6H,2-5,7H2,1H3

InChIKey

FLQSRSQNICPZIH-UHFFFAOYSA-N

SMILES

N1(S(C)(=O)=O)CCC(N)CC1

Safety

Hazard Codes 

Xi

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

1-(METHYLSULFONYL)PIPERIDIN-4-AMINE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 1-methylsulfonyl-4-aminopiperidine from 1-MS-4-Boc-aminopiperidine: 6.30 g (22.63 mmol) of tert-butyl (1-methylsulfonyl-piperidin-4-yl)-carbamate was dissolved in 74 mL of dichloromethane (DCM) followed by the addition of 17.4 mL (226 mmol) of trifluoroacetic acid (TFA). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was diluted with diethyl ether at 40 °C, the precipitate was collected by filtration, washed with water and dried. The dried product was dissolved in methanol (MeOH), polymer-loaded bicarbonate (PL-HCO3 MP resin, Agilent Technologies) was added, and the suspension was stirred for several minutes. The resin was subsequently removed by filtration and the solvent was removed by distillation under reduced pressure to give 4.00 g of 1-methylsulfonyl-piperidin-4-ylamine. Yield: 99%; ESI-MS: 179 [M + H]+; HPLC (retention time): 0.26 min (Method E).

References

[1] Patent: US8865744, 2014, B1. Location in patent: Page/Page column 26
[2] Patent: WO2014/184327, 2014, A1. Location in patent: Page/Page column 27
[3] Patent: US2015/225367, 2015, A1. Location in patent: Paragraph 0406
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6549 - 6560
[5] Bioorganic Chemistry, 2015, vol. 61, p. 21 - 27