1-(2-Chloroethyl)pyrrolidine Hydrochloride Chemical Properties

Melting point:

167-170 °C(lit.)

Boiling point:

237°C(lit.)

Density 

0.4[at 20℃]

vapor pressure 

1.64hPa at 25℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Water (Slightly)

form 

Crystalline Powder or Crystals

color 

White to off-white

Water Solubility 

Soluble

Sensitive 

Hygroscopic

BRN 

3677061

InChI

InChI=1S/C6H12ClN.ClH/c7-3-6-8-4-1-2-5-8;/h1-6H2;1H

InChIKey

FSNGFFWICFYWQC-UHFFFAOYSA-N

SMILES

N1(CCCl)CCCC1.[H]Cl

LogP

0.736 at 25℃

CAS DataBase Reference

7250-67-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/22

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

UY0703150

HS Code 

29339900

MSDS

• Language:English Provider:2-Pyrrolidinoethyl chloride hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-(2-Chloroethyl)pyrrolidine Hydrochloride Usage And Synthesis

Chemical Properties

white to off-white crystals or crystalline powder

Uses

1-(2-Chloroethyl)pyrrolidine Hydrochloride is a haloalkyl-substituted pyrrolidine used in the preparation of various pharmaceutical compounds, such as the estrogen receptor antagonist Nafoxidine (N212800) and its analogs.

Synthesis

The general procedure for the synthesis of N-(2-chloroethyl)pyrrolidine hydrochloride from tetrandrine and 2-chloroethanol was as follows: 165 mL (2 mol) of tetrandrine, 67 mL (1 mol) of 2-chloroethanol, and 200 mL of toluene were added sequentially to a reaction flask. The mixture was heated to reflux temperature and kept reacting for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solid product was isolated. The solid was collected by diafiltration and the filter cake was washed with 20 mL of toluene. The temperature of the filtrate was controlled at about 75 °C and 200 mL of thionyl chloride was slowly added dropwise. After the dropwise addition was completed, the reaction was continued at reflux for 2 hours. At the end of the reaction, the mixture was cooled to room temperature and subsequently concentrated to dryness under reduced pressure. The resulting residue was recrystallized from anhydrous ethanol to give 105 g of white solid product in 62.3% yield. The melting point of the product was 198-203 °C.

Purification Methods

Purify the hydrochloride by recrystallisation from isopropanol/di-isopropyl ether (charcoal) and recrystallise it twice more. The free base, b 55-56o/11mm, 60-63o/23mm and 90o/56mm, is relatively unstable and should be converted to the hydrochloride immediately, by dissolving in isopropanol and bubbling dry HCl through the solution at 0o, filtering off the hydrochloride and recrystallising it. The picrate has m 107.3-107.8o (from EtOH) [Cason J Org Chem 24 247 1959, Wright et al. J Am Chem Soc 70 3098 1948]. [Beilstein 20 III/IV 66.]

References

[1] Patent: US2013/85140, 2013, A1. Location in patent: Paragraph 0068; 0069
[2] Patent: CN104710394, 2017, B. Location in patent: Paragraph 0033-0035

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