4-(MORPHOLINOMETHYL)BENZOIC ACID

4-(MORPHOLINOMETHYL)BENZOIC ACID Property

Melting point:

179-183°C

Boiling point:

369.8±32.0 °C(Predicted)

Density 

1.233±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.00±0.10(Predicted)

color 

Off-White to Beige

Sensitive 

Hygroscopic

CAS DataBase Reference

62642-62-0

Safety

Hazard Codes 

Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2916310090

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

4-(MORPHOLINOMETHYL)BENZOIC ACID Chemical Properties,Usage,Production

Uses

4-?(Morpholinomethyl)?benzoic Acid is a reactant used in the synthesis of sirtuin 2 inhibitors, used in the treatment of parkinsons.

Synthesis

General procedure for the synthesis of 4-morpholinomethylbenzoic acid from methyl 4-(morpholinomethyl)benzoate: to a stirred solution of methyl 4-(morpholinomethyl)benzoate (4.0 g, 17.0020 mmol, 1.0 eq.) in methanol (40 mL) was added slowly at 0 °C an aqueous 1N NaOH solution (136.0 mL, 136.0 mmol, 8.0 equivalent). The reaction mixture was stirred at room temperature overnight. The progress of the reaction was monitored by TLC and after confirming the completion of the reaction, the reaction mixture was cooled to 0 °C and neutralized with 1N HCl to pH neutral. Subsequently, the solvent was removed by evaporation under reduced pressure. Methanol (40 mL) and dichloromethane (60 mL) were added to the resulting solid and stirred at room temperature for 25 minutes. The mixture was filtered and the filtrate was evaporated under reduced pressure to recover the product. The above extraction and evaporation process was repeated twice to finally obtain a white solid product (3.0 g, yield: 79.57%), which could be used in the next reaction without further purification. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3) and ESI-MS: 1H NMR δ 8.04 (d, J = 8.1 Hz, 2H), 7.50 (d, J = 8.1 Hz, 2H), 3.81 (m, 4H), 3.71 (s, 2H), 2.62 (m, 4H); ESI-MS: m/z 222.01 (M + H)+.

References

[1] Patent: WO2018/29604, 2018, A1. Location in patent: Page/Page column 45
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 179 - 190