4-(4'-Bromophenyl)piperidine Chemical Properties

Melting point:

144-146 °C

Boiling point:

307.6±42.0 °C(Predicted)

Density 

1.313±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

10.14±0.10(Predicted)

color 

Pale yellow

InChI

InChI=1S/C11H14BrN/c12-11-3-1-9(2-4-11)10-5-7-13-8-6-10/h1-4,10,13H,5-8H2

InChIKey

ZKABWLFDCJKQRE-UHFFFAOYSA-N

SMILES

N1CCC(C2=CC=C(Br)C=C2)CC1

CAS DataBase Reference

80980-89-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-52

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933399990

4-(4'-Bromophenyl)piperidine Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-(4-bromophenyl)piperidine from 4-(4-bromophenyl)-1,2,3,6-tetrahydropyridine: to a solution of 4-(4-bromophenyl)-1,2,3,6-tetrahydropyridine (0.90 g, 3.78 mmol) in anhydrous methanol (20 mL) and triethylamine (2 mL), the Rh/C catalyst (0.060 g, J. Bishop & Co. Platinum). The reaction mixture was placed in a hydrogen atmosphere (100 psi) and stirred at room temperature for 24 hours. Upon completion of the reaction, the mixture was filtered through a Celite?(Sigma Aldrich, St. Louis, MO) filter cake and the filtrate was concentrated to afford 4-(4-bromophenyl)piperidine as a white solid (0.91 g, 98% yield). The product was confirmed by 1H NMR (400 MHz, MeOD): δ 1.55-1.59 (2H, m), 1.61-1.70 (2H, m), 2.55-2.56 (1H, m), 2.64-2.70 (2H, m), 3.09-3.06 (2H, m), 7.13 (2H, J = 8.0 Hz, d), 7.31 ( 2H, J = 8.0 Hz, d).13C NMR (100 MHz, MeOD): δ 32.7, 41.4, 45.6, 119.4, 126.4, 128.2, 128.5, 131.2, 145.3. m/z of mass spectrum (ESI-MS): 241 [M+H]+.

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6149 - 6168
[2] Patent: WO2017/53769, 2017, A1. Location in patent: Paragraph 0117; 0118

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