1-(aminomethyl)cyclopentanol hydrochloride

1-(aminomethyl)cyclopentanol hydrochloride Property

Melting point:

190℃

storage temp. 

Inert atmosphere,Room Temperature

Appearance

Off-white to light brown Solid

Safety

HS Code 

2922190090

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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

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

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

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

1-(aminomethyl)cyclopentanol hydrochloride Chemical Properties,Usage,Production

Uses

1-(Aminomethyl)cyclopentanol Hydrochloride is used for preparation and inhibition of phenylethanolamine N-methyltransferase. It is also used for preparation of sulfonyl benzimidazole derivatives useful in treatment of diseases-mediated by CB2 receptor.

Synthesis

The general procedure for the synthesis of 1-(aminomethyl)cyclopentanol hydrochloride from 1-hydroxycyclopentanecarbonitrile was as follows: to a mixture of cyclopentanone (5.50 g, 65.0 mmol) and ZnBr2 (0.20 g, 8.00 mmol) under cooling in an ice bath, TMSCN (10.0 mL, 73.4 mmol) was slowly added, and the reaction was subsequently stirred at room temperature for mixture for 12 hours. The resulting cyanohydrin solution was slowly added dropwise to a suspension of LiAlH4 (8.34 g, 219 mmol) in THF (30.0 mL) at 0 °C, and the mixture was then heated to reflux for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and water (10.0 mL), 4M NaOH aqueous solution (10.0 mL), and water (10.0 mL) were added slowly and sequentially under vigorous stirring. Insoluble material was removed by filtration through a diatomaceous earth pad, and the organic phase was separated and dried with KOH. The dried organic phase was decanted, dried over Na2SO4, filtered and concentrated. The residue was dissolved in MTBE (100 mL), a dioxane solution (10.0 mL) of 4N HCl was added, and stirred at room temperature for 30 minutes. The resulting white solid precipitate was collected by filtration through a sintered funnel to afford the target product 1-(aminomethyl)cyclopentanol hydrochloride (6.68 g, 68% yield).

References

[1] Patent: US2017/217986, 2017, A1. Location in patent: Paragraph 0564; 0565