1-Boc-4-Methylaminopiperidine Chemical Properties

Boiling point:

289.0±33.0 °C(Predicted)

Density 

1.005 g/mL at 25 °C

refractive index 

n20/D1.468

Flash point:

>110℃

storage temp. 

2-8°C

pka

10.19±0.20(Predicted)

form 

clear liquid

color 

Colorless to Almost colorless

InChI

InChI=1S/C11H22N2O2/c1-11(2,3)15-10(14)13-7-5-9(12-4)6-8-13/h9,12H,5-8H2,1-4H3

InChIKey

CZYUGTLMFHDODF-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(NC)CC1

CAS DataBase Reference

147539-41-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,T

Risk Statements 

36/37/38-50-25

Safety Statements 

26-61-45-36/37/39

RIDADR 

2810

WGK Germany 

3

F 

10-34

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29339900

1-Boc-4-Methylaminopiperidine Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

1-Boc-4-(methylamino)piperidine is used as an organic chemical synthesis intermediate.

Uses

1-Boc-4-methylaminopiperidine is a derivatieve of 3-Methylaminopiperidine Dihydrochloride, which is a a key intermediate for the antibacterial agent balofloxacin.

Synthesis

GENERAL STEPS: To a suspension of N-Boc-4-piperidone (10.00 g, 50.19 mmol) in ethanol (75 mL) was added 10% Pd/C catalyst (1.00 g, 10 wt%), methylamine (33% ethanol solution, 27 mL, 0.20 mol) and formic acid (46 mg, 1.00 mmol). The reaction mixture was placed in an autoclave, sealed under a hydrogen atmosphere at 4 MPa and stirred at 50°C overnight. After completion of the reaction, it was cooled to room temperature and filtered to remove the catalyst. The filtrate was concentrated in vacuum to afford 1-Boc-4-(methylamino)piperidine as a pale yellow liquid (10.70 g, 99% yield). Mass spectrum (ESI, cation mode) m/z: 215.3 [M + H]+; 1H NMR (400 MHz, CDCl3): δ (ppm) 4.01 (m, 2H), 2.79 (m, 2H), 2.48 (m, 1H), 2.42 (s, 3H), 1.83 (m, 2H), 1.44 (s, 9H), 1.28-1.15 (m, 2H).

References

[1] Patent: WO2015/73267, 2015, A1. Location in patent: Paragraph 332
[2] Patent: CN104650092, 2017, B. Location in patent: Paragraph 0533-0536
[3] Patent: US2006/160786, 2006, A1. Location in patent: Page/Page column 32
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4281 - 4285
[5] Patent: WO2005/7645, 2005, A1. Location in patent: Page 77

1-Boc-4-Methylaminopiperidine(147539-41-1)Related Product Information

• tert-butyl 4-(difluoroMethyl)piperidine-1-carboxylate
• 1-Boc-4-(aminomethyl)piperidine
• 1-TERT-BUTYL 2-METHYL PIPERIDINE-1,2-DICARBOXYLATE
• N-BOC-3-Aminopiperidine
• 1-BOC-3-PIPERIDINECARBOXALDEHYDE
• N-Boc-4-piperidinemethanol
• (+/-)-1-N-BOC-PIPERIDINE-2-CARBOXAMIDE
• 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde
• N-BOC-piperidine-4-carboxylic acid
• N-Boc-2-piperidinecarboxylic acid
• Ethyl N-Boc-piperidine-4-carboxylate
• Ethyl 1-Boc-piperidine-2-carboxylate
• 1-Boc-3-hydroxypiperidine
• N-Boc-Piperidine-4-carboxylic acid methyl ester
• N-Boc-piperidine-3-methanol
• N-Boc-piperidine-2-methanol
• TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE
• 1-N-BOC-PIPERIDINE-3-CARBOXAMIDE