1-N-Boc-3-(S)-Methylamino-piperidine Chemical Properties

Boiling point:

289℃

Density 

1.01

Flash point:

129℃

refractive index 

1.4600

storage temp. 

2-8°C

form 

Liquid

pka

10.10±0.20(Predicted)

color 

Colorless to yellow

optical activity

13.3°(C=1.00g/100mL CHCL3)

Sensitive 

Moisture Sensitive

Safety Information

Hazard Codes 

T,N

Risk Statements 

25-36-50

Safety Statements 

26-45-61

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

6.1

HS Code 

2933399990

1-N-Boc-3-(S)-Methylamino-piperidine Usage And Synthesis

Synthesis

General procedure for the synthesis of 1-N-BOC-3-(S)-methylaminopiperidine from formaldehyde and (S)-1-Boc-3-aminopiperidine: tert-butyl (5.0 g, 25 mmol) of (S)-3-aminopiperidine-1-carboxylate (5.0 g, 25 mmol) was added to a stirred aqueous formaldehyde (1.85 mL, 25 mmol, 37%) and suspension of molecular sieves in methanol and the reaction mixture was stirred at room temperature (24 °C) the reaction mixture was stirred for 24 hours. Subsequently, sodium borohydride (1.52 g, 40 mmol) was slowly added to the above mixture at room temperature and stirring was continued for 16 hours. Upon completion of the reaction, the reaction was quenched by the addition of ice water (30 mL) and extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to afford 3.0 g of the crude product (S)-tert-butyl 3-(methylamino)piperidine-1-carboxylate as a light yellow liquid, which was used directly in the next step of the reaction.1H NMR (400 MHz, CDCl3) δ ppm: 1.38 (s, 9H), 1.5-1.7 (m, 4H), 1.71-1.90 (m 2H), 2.18-2.27 (m, 3H), 2.75-2.90 (m, 1H), 3.50-3.92 (m, 2H).

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 1061 - 1073
[2] Patent: WO2018/2437, 2018, A1. Location in patent: Page/Page column 99

1-N-Boc-3-(S)-Methylamino-piperidine(912368-73-1)Related Product Information

• R-3-Dimethylamino-N-Boc-piperidine
• S-3-(Carbamylamino)-N-Boc-piperidine
• (S)-1-Boc-3-(Cbz-amino)-piperidine
• (1S,4S)-2-BOC-2,5-DIAZABICYCLO(2.2.2)OCTANE
• 1-N-Boc-3-(S)-Methylamino-piperidine
• (S)-1-Boc-3-(2,2,2-Trifluoro-acetylamino)-piperidine
• (1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.2]OCTANE HYDROCHLORIDE
• (S)-1-BOC-3-N-(PYRIDIN-4-YLMETHYL)-AMINO-PIPERIDINE