1-Benzyl-3-piperidinol Chemical Properties

Boiling point:

140-142°C 6mm

Density 

1,056 g/cm³

refractive index 

n20/D 1.549

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

clear liquid

pka

14.82±0.20(Predicted)

color 

Colorless to Light yellow

Sensitive 

Hygroscopic

BRN 

135964

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

InChIKey

UTTCOAGPVHRUFO-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)CCCC(O)C1

CAS DataBase Reference

14813-01-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-36/37/38

Safety Statements 

26-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

2

HS Code 

29333990

MSDS

• Language:English Provider:1-N-Benzyl-3-hydroxy-piperidine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Benzyl-3-piperidinol Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

Reactant for bioresolution of tertiary amino ester protic ionic liquids using subtilisin

Reactant for synthesis of:

• Muscarinic M3 selective antagonists
• Rho kinase inhibitors
• Piperidine derivatives for investigations into α-adrenoreceptor direct activation

Synthesis

General procedure for the synthesis of 1-benzyl-3-piperidinol from 1-benzyl-3-piperidone: first, N-benzyl-3-piperidone hydrochloride was converted to a free base by the addition of an aqueous solution of K2CO3, which was subsequently extracted with ethyl acetate. Next, sodium borohydride (NaBH4) (0.438 g, 11.57 mmol) was slowly added to an ethanol solution containing N-benzyl-3-piperidone (2.19 g, 11.57 mmol) over 10 min. The reaction mixture was stirred overnight at room temperature and then concentrated under vacuum. The concentrated residue was dissolved in 1.0 N HCl and washed twice with diethyl ether. Afterwards, the aqueous phase was adjusted to pH 12 with 3.0N KOH and extracted three times with dichloromethane. The organic phases were combined and dried with Na2SO4, followed by vacuum concentration. The purity of the crude product was 100% (1.900 g, 86% yield) by IC/MS (EI) analysis: m/z 192.3 (M+1).

Waste Disposal

2,4-Dichloro-5-methoxypyrimidine is a halogen-containing aromatic ring organic compound, which is more harmful to the water environment. Therefore, undiluted or large amounts of 2,4-dichloro-5-methoxypyrimidine should not be exposed to groundwater, waterways, or sewage systems.

References

[1] Patent: WO2005/26145, 2005, A2. Location in patent: Page/Page column 98
[2] Process Biochemistry, 2017, vol. 56, p. 90 - 97

1-Benzyl-3-piperidinol(14813-01-5)Related Product Information

• Benzyl alcohol
• Benzyl bromide
• CHLOROPHOSPHONAZO III
• Benzyl isocyanate
• Benzyl chloride
• Haloperidol
• 4-[4-Chloro-3-(trifluoromethyl)phenyl]-4-piperidinol
• Benzyltriethylammonium chloride
• 2,2,6,6-Tetramethyl-4-piperidinol
• Benzyl benzoate
• Benzyl nicotinate
• 3-Hydroxypiperidine
• 3-benzyloxypyridine
• Benidipine Impurity 6
• Benidipine Impurity 22
• benidipine
• Benidipine Impurity
• N-Benzyl-4-piperidone