(3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine Chemical Properties

Melting point:

97-101 °C

alpha 

-38 º (c=1, MeOH)

Boiling point:

300.3±42.0 °C(Predicted)

Density 

1.092±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

14.93±0.10(Predicted)

color 

White to Almost white

optical activity

Consistent with structure

InChI

InChI=1S/C13H18FNO/c1-15-7-6-13(11(8-15)9-16)10-2-4-12(14)5-3-10/h2-5,11,13,16H,6-9H2,1H3/t11-,13-/m0/s1

InChIKey

CXRHUYYZISIIMT-AAEUAGOBSA-N

SMILES

N1(C)CC[C@@H](C2=CC=C(F)C=C2)[C@H](CO)C1

CAS DataBase Reference

105812-81-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

N-Xn,N,Xn

Risk Statements 

51/53-41-22

Safety Statements 

61-39-26-22-37/39-24

RIDADR 

UN3077

HazardClass 

9

PackingGroup 

III

HS Code 

29333999

MSDS

• Language:English Provider:ACROS

(3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

An intermediate in the synthesis of Paroxetine, a selective serotonin reuptake inhibitor.

Uses

An intermediate in the synthesis of Paroxetine (P205750), a selective serotonin reuptake inhibitor.

Synthesis

The general procedure for the synthesis of (3S,4R)-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine from the compound (CAS:335158-58-2) is as follows: in a 500 mL round-bottomed flask equipped with a stirrer, a condenser and a thermometer, 31.4 g of trans-N-methyl-4'-fluorophenyl-3-methoxypiperidine and 100 mL of tetrahydrofuran were added . Subsequently, 3.31 g of lithium aluminum hydride was slowly added to the reaction system while the reaction temperature was controlled to be maintained at 10 °C. After the addition was completed, the reaction mixture was continued to be stirred until the reaction was completed. After the reaction was completed, 50 mL of distilled water and 30 mL of 10% aqueous sodium hydroxide solution were slowly added and stirring was continued for 30 minutes. Next, 200 mL of ethyl acetate was added to the reaction mixture and stirred for another 30 minutes. The organic and aqueous phases were separated and the solvent and low-boiling organic material were removed by distillation. The residue was recrystallized by a mixture of toluene and n-heptane to afford the target product trans-N-methyl-4'-fluorophenyl-3-hydroxymethylpiperidine (yield: 78.4%, purity: 99.3%). The Rf value of the product was 0.3 (unfolding agent: dichloromethane/methanol, 4:1).1H NMR (CDCl3, 200 MHz) data were as follows: δ 7.18 (t, 2H, J = 8.7 Hz); 6.98 (t, 2H, J = 8.7 Hz); 3.39 (dd, 1H, J = 10.6 Hz, J = 2.8 Hz); 3.25-3.14 ( m, 2H); 2.93 (d, 1H, J = 10.8 Hz); 2.70 (s, 1H); 2.31 (s, 3H); 2.27-2.21 (m, 1H); 2.09-1.75 (m, 5H).

References

[1] Patent: WO2004/5254, 2004, A1. Location in patent: Page 9
[2] Patent: WO2005/63707, 2005, A1. Location in patent: Page 26
[3] Patent: WO2005/63707, 2005, A1. Location in patent: Page 27

(3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine(105812-81-5)Related Product Information

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