1-TERT-BUTOXYCARBONYL-4-(CYCLOPROPYLAMINO)PIPERIDINE

1-TERT-BUTOXYCARBONYL-4-(CYCLOPROPYLAMINO)PIPERIDINE Property

Boiling point:

329.7±35.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

8.89±0.20(Predicted)

form 

oil

color 

Clear colourless

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

1-TERT-BUTOXYCARBONYL-4-(CYCLOPROPYLAMINO)PIPERIDINE Chemical Properties,Usage,Production

Synthesis

A methanol (40 mL) solution of tert-butyl 4-oxopiperidine-1-carboxylate (5.0 g, 25.1 mmol) was added to the reaction flask, followed by cyclopropylamine (1.4 g, 25.1 mmol), triethylamine (10.0 mL, 75.3 mmol) and zinc chloride (0.3 g, 2.5 mmol). The reaction mixture was stirred at 60 °C for 7 h. Then sodium cyanoborohydride (4.8 g, 75.3 mmol) was added in batches. The reaction mixture was continued to be stirred at 25 °C for 17 hours. Upon completion of the reaction, the solvent was removed under vacuum and the residue was partitioned between water (250 mL) and ethyl acetate (200 mL). The aqueous layer was further extracted with ethyl acetate (2 x 200 mL) and the organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography (basic activated alumina, eluent: 10% to 30% hexane solution of ethyl acetate) to afford the target product tert-butyl 4-(cyclopropylamino)piperidine-1-carboxylate (5.3 g, 88% yield) as a gel. The product data are shown in Table 2.

References

[1] Patent: WO2017/21730, 2017, A1. Location in patent: Page/Page column 46
[2] Journal of Medicinal Chemistry, 1996, vol. 39, # 19, p. 3769 - 3789
[3] Patent: WO2010/52255, 2010, A1. Location in patent: Page/Page column 53-54
[4] Patent: WO2007/16610, 2007, A2. Location in patent: Page/Page column 57; 58
[5] Patent: EP3147283, 2017, A1. Location in patent: Paragraph 0106