Methyl 1-benzyl-4-oxo-3-piperidine-carboxylate hydrochloride Chemical Properties

Melting point:

185 °C (dec.)(lit.)

storage temp. 

Inert atmosphere,Room Temperature

form 

Crystalline Powder

color 

White to pink

Sensitive 

Hygroscopic

InChI

InChI=1S/C14H17NO3.ClH/c1-18-14(17)12-10-15(8-7-13(12)16)9-11-5-3-2-4-6-11;/h2-6,12H,7-10H2,1H3;1H

InChIKey

BRADBAOVPACOQQ-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)CCC(=O)C(C(OC)=O)C1.[H]Cl

CAS DataBase Reference

3939-01-3(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Methyl 1-benzyl-4-oxo-3-piperidine-carboxylate hydrochloride Usage And Synthesis

Chemical Properties

white to pink crystalline powder

Uses

Methyl 1-benzyl-4-oxo-3-piperidinecarboxylate, HCl

Uses

Methyl 1-benzyl-4-oxo-3-piperidinecarboxylate hydrochloride (1-Benzyl-3-carbomethoxy-4-piperidone hydrochloride) may be used in chemical synthesis.

Synthesis

Step A: Synthesis of methyl 4-oxo-1-(phenylmethyl)-3-piperidinecarboxylate hydrochloride. A solution was prepared by dissolving 1-benzyl-4-piperidone (56.5 kg, 1.0 eq.) in toluene (189 L) at 15 °C to 25 °C. In another reactor, toluene (659L), potassium tert-butoxide (71.9 kg, 2.25 eq.) and dimethyl carbonate (51.5 kg, 2.0 eq.) were added at 15 °C to 25 °C to form a slurry. The slurry was heated to 80°C to 90°C. A toluene solution of 1-benzyl-4-piperidone was slowly added to the slurry over a period of 60 to 90 minutes. After 90 minutes of reaction, the mixture was cooled to below 15°C. The reaction was quenched with acetic acid (38.5 kg, 2.25 eq.) and water (367 L). The two phases were separated and the organic layer was filtered to remove solids. The organic filtrate was concentrated by distillation under reduced pressure to about 150 L. Toluene (799 L) was added to the concentrate and hydrogen chloride gas (11.0 kg, 1.05 eq.) was passed through to form a hydrochloride precipitate. The slurry was stirred at 10°C to 15°C for 30 minutes. The solid was collected by filtration, washed with hexane (~130 L) and dried under vacuum to give 79.4 kg of methyl 4-oxo-1-(phenylmethyl)-3-piperidinecarboxylate hydrochloride in 97.8% yield. Elemental analysis (C14H17NO3-HCl) Calculated values: C 59.3, H 6.39, N 4.94; measured values: C 59.7, H 6.65, N 4.85.

References

[1] Patent: EP1031575, 2000, A1
[2] Patent: US2002/2283, 2002, A1

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