(R)-(-)-1-Benzyl-3-hydroxypiperidine Chemical Properties

Boiling point:

275 °C (lit.)

alpha 

-12 º (C=1 IN MEOH)

Density 

1.07 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.547(lit.)

Flash point:

>230 °F

storage temp. 

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

form 

clear liquid

pka

14.82±0.20(Predicted)

color 

Light orange to Yellow to Green

optical activity

[α]24/D 12°, c = 1 in methanol

InChI

InChI=1S/C12H17NO/c14-12-7-4-8-13(10-12)9-11-5-2-1-3-6-11/h1-3,5-6,12,14H,4,7-10H2/t12-/m1/s1

InChIKey

UTTCOAGPVHRUFO-GFCCVEGCSA-N

SMILES

N1(CC2=CC=CC=C2)CCC[C@@H](O)C1

CAS DataBase Reference

91599-81-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-36/37/38

Safety Statements 

26-45

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

(R)-(-)-1-Benzyl-3-hydroxypiperidine Usage And Synthesis

Uses

(R)-1-Benzyl-3-piperidinol is a benzylpiperidine derivative with hypotensive affects. (R)-1-Benzyl-3-piperidinol is used in the preparation of in vivo probes for measuring endogenous acetylcholine lev els.

Synthesis

General procedure for the synthesis of (R)-(-)-1-benzyl-3-hydroxypiperidine using 1-benzyl-3-piperidone as starting material: a reaction mixture was prepared in 1 mL of potassium phosphate buffer (100 mM, pH 7.0) containing 200 mM 1-benzyl-3-piperidone, 1 mM NAD+, 5% (v/v) 2-propanol, and 10 mg of the crude enzyme READH. The reaction mixture warmed at 50°C. For ChKRED20, the reaction conditions were adjusted to 40% (v/v) 2-propanol and 40 °C reaction temperature. The reaction progress was monitored by TLC and the reaction was terminated by extraction with 1 mL of methyl tert-butyl ether. The organic phase was dried with anhydrous sodium sulfate and concentrated. The conversion and enantiomeric excess were determined by chiral HPLC. The products were purified by silica gel column chromatography and structurally characterized by NMR analysis, spinometry and mass spectrometry.

References

[1] Process Biochemistry, 2017, vol. 56, p. 90 - 97

(R)-(-)-1-Benzyl-3-hydroxypiperidine(91599-81-4)Related Product Information

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