3-[(4-METHYLPIPERAZIN-1-YL)METHYL]BENZONITRILE

3-[(4-METHYLPIPERAZIN-1-YL)METHYL]BENZONITRILE Property

storage temp. 

2-8°C

Safety

HS Code 

2933599590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

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

P310Immediately call a POISON CENTER or doctor/physician.

3-[(4-METHYLPIPERAZIN-1-YL)METHYL]BENZONITRILE Chemical Properties,Usage,Production

Uses

3-?((4-?Methylpiperazin-?1-?yl)?methyl)?benzonitrile is involved in the preparation of N-Hydroxyphenylacrylamides and N-Hydroxypyridin-2-ylacrylamides as novel histone deacetylase inhibitors.

Synthesis

General procedure for the synthesis of 3-((4-methylpiperazin-1-yl)methyl)benzonitrile from N-methylpiperazine and 3-cyanobenzaldehyde: Step 1: 3-Formylbenzonitrile (1.5 g, 11.45 mmol), N-methylpiperazine (1.49 g, 14.9 mmol) and sodium triacetoxyborohydride (3.63 g, 17.18 mmol) were dissolved in dichloromethane (75 ml), acetic acid (0.851 ml, 14.9 mmol) was added and the reaction was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with 1 M sodium carbonate solution. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (eluent: dichloromethane/methanol/ammonia = 97:3:0.5) to give 3-(4-methylpiperazin-1-ylmethyl)benzonitrile 1.7 g in 70% yield.

References

[1] Patent: WO2007/113249, 2007, A2. Location in patent: Page/Page column 60-61
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 822 - 839
[3] Patent: EP2033956, 2009, A1. Location in patent: Page/Page column 13
[4] Patent: WO2006/130075, 2006, A1. Location in patent: Page/Page column 25-26