4-N-Boc-4-N-Methyl-aminopiperidine Chemical Properties

Melting point:

50°C(lit.)

Boiling point:

287.9±29.0 °C(Predicted)

Density 

1.01±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

crystalline powder

pka

10.05±0.10(Predicted)

color 

White

InChI

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

InChIKey

DJJOYDXRUBOZON-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)N(C)C1CCNCC1

CAS DataBase Reference

108612-54-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-28-36-44

Hazard Note 

Irritant

HS Code 

29339900

4-N-Boc-4-N-Methyl-aminopiperidine Usage And Synthesis

Uses

4-N-Boc-4-N-methyl-aminopiperidine, or Tert-butyl methyl(piperidin-4-yl)carbamate (TBMPC) is a derivative of piperidine and is structurally similar to other carbamates. It inhibits the enzyme cyclooxygenase and modulates the activity of the neurotransmitter GABA. This compound has demonstrated anticonvulsant and anti-inflammatory activity. TBMPC has been studied for its potential use in various in vivo and in vitro applications. It has been reported to reduce the frequency and duration of seizures in animal models and reduce the production of pro-inflammatory cytokines in cell culture.

Synthesis

General procedure for the synthesis of 4-N-tert-butoxycarbonyl-4-N-methylaminopiperidine from tert-butyl (1-benzylpiperidin-4-yl)(methyl)carbamate: 10% (w/w) humidity Pd/C catalyst (1.1 g) was added to a 250 mL three-necked flask. After sealing the flask, three evacuations and backfilling with nitrogen were performed. Subsequently, a methanol solution of 1-benzyl-4-(N-Boc-N-methyl)aminopiperidine (10.7 g, 35.2 mmol) was added to the flask. The operation was again carried out with three evacuations and backfilled with hydrogen. The reaction mixture was stirred at room temperature for three days, during which the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, three evacuations and backfilling with nitrogen were performed. The reaction mixture was filtered and the filtrate was concentrated under vacuum to give 6.8 g of the target product 4-N-tert-butoxycarbonyl-4-N-methylaminopiperidine as a white solid in 90% yield.

References

[1] Journal of Medicinal Chemistry, 1999, vol. 42, # 24, p. 4981 - 5001
[2] Tetrahedron Letters, 2017, vol. 58, # 20, p. 1976 - 1979
[3] Patent: US2012/71461, 2012, A1. Location in patent: Page/Page column 144

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