1-(2,6-DICHLOROBENZYL)PIPERAZINE

1-(2,6-DICHLOROBENZYL)PIPERAZINE Property

Melting point:

54-62 °C

Boiling point:

332.4±37.0 °C(Predicted)

Density 

1.252±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

9.02±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C11H14Cl2N2/c12-10-2-1-3-11(13)9(10)8-15-6-4-14-5-7-15/h1-3,14H,4-8H2

InChIKey

WQTPGHSKQDVCQQ-UHFFFAOYSA-N

SMILES

N1(CC2=C(Cl)C=CC=C2Cl)CCNCC1

CAS DataBase Reference

102292-50-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-(2,6-DICHLOROBENZYL)PIPERAZINE Chemical Properties,Usage,Production

Synthesis

1. Dissolve piperazine (112 mmol, 6.0 eq.) in THF (180 mL) at 0 °C to prepare a solution. 2. 2,6-dichlorobenzyl bromide (4.5 g, 18.8 mmol) was dissolved in THF (20 mL) to prepare a solution and slowly added dropwise to the THF solution of piperazine over 10 minutes. 3. After the dropwise addition was completed, the reaction mixture was slowly warmed to room temperature and stirred continuously for 24 hours. 4. Upon completion of the reaction, the THF solvent was removed by distillation under reduced pressure. 5. The crude product was resuspended in a mixture of dichloromethane (DCM) and water and extracted twice with DCM. 6. The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated. 7. The crude product was purified using combiflash fast chromatography eluting with a gradient of 0 to 20% methanol in DCM to afford the target compound 1-(2,6-dichlorobenzyl)piperazine (2.3 g, 50% yield). 8. The structure of the product was confirmed by 1H NMR, 13C NMR and HRMS. 1H NMR (400 MHz, methanol-d4) δ 7.62-7.30 (m, 2H), 7.23 (dd, J = 8.7, 7.4 Hz, 1H), 3.74 (s, 2H), 2.92-2.69 (m, 4H), 2.56 (t, J = 4.9 Hz, 4H). 13C NMR (101 MHz, MeOD) δ 136.76, 133.67, 129.18, 128.24, 56.55, 53.41, 44.95. HRMS (m/z): [M+] calculated value C11H14Cl2N2 245.15, measured value 245.06.

References

[1] Patent: WO2015/184349, 2015, A2. Location in patent: Paragraph 0221
[2] Patent: WO2016/176338, 2016, A1. Location in patent: Paragraph 0132
[3] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 22 - 38