4-AMINO-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER Chemical Properties

Melting point:

68 °C(dec.)

Boiling point:

367.2±42.0 °C(Predicted)

Density 

1.151±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to lump

pka

10.07±0.20(Predicted)

color 

White to Light yellow

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C13H18N2O2/c14-12-6-8-15(9-7-12)13(16)17-10-11-4-2-1-3-5-11/h1-5,12H,6-10,14H2

InChIKey

YYIQGSYCCNQAGV-UHFFFAOYSA-N

SMILES

N1(C(OCC2=CC=CC=C2)=O)CCC(N)CC1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-37-60

RIDADR 

UN3259

HazardClass 

8

HS Code 

29333990

4-AMINO-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER Usage And Synthesis

Uses

It is an important raw material and intermediate used in organic synthesis agrochemical, pharmaceutical and dyestuff field.

Synthesis

General procedure for the synthesis of 1-Cbz-4-aminopiperidine (benzyl 4-aminopiperidine-1-carboxylate) from 1-Cbz-4-BOC-aminopiperidine: 4-(N-BOC amino)-Cbz piperidine (24.4 kg, 73.42 mol), THF (65 kg), and 5M HCl (23.0 kg, 110.13 mol) were mixed and heated to 30-35 °C for 2 h. The reaction was then continued at 55 °C overnight. After completion of the reaction, the mixture was cooled to 100 °C and dichloromethane (97 kg) and 10 M NaOH (7.97 kg, 145.12 mol) were added, controlling the temperature below 25 °C. After partitioning, the organic phase was washed with 25 wt% NaCl solution (27.5 kg). The washed organic phase was concentrated by distillation at atmospheric pressure to a volume of about 70 L. Subsequently, dichloromethane (162 kg) was added and concentrated by distillation again to a volume of about 120 L to give a dichloromethane solution of the title product 1-Cbz-4-aminopiperidine (17.2 kg, 100% yield). The structure of the product was confirmed by 1H NMR (CDCl3): δ 7.33 (5H, m), 5.14 (2H, s), 4.14 (2H, br s), 2.87 (3H, m), 1.83 (2H, m), 1.66 (3H, m), 1.28 (2H, m).

References

[1] Patent: WO2009/91856, 2009, A2. Location in patent: Page/Page column 63-64

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