4-(MORPHOLINOMETHYL)BENZOIC ACID Chemical Properties

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 Information

Hazard Codes 

Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2916310090

4-(MORPHOLINOMETHYL)BENZOIC ACID Usage And Synthesis

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

4-(MORPHOLINOMETHYL)BENZOIC ACID(62642-62-0)Related Product Information

• 4-(PIPERIDIN-4-YL)-MORPHOLINE
• 4-(MORPHOLINOMETHYL)BENZOIC ACID
• CHEMBRDG-BB 6555065
• 3-BROMO-4-(MORPHOLINOMETHYL)BENZOIC ACID
• 4-[(2,6-dimethylmorpholin-4-yl)methyl]benzoic acid
• 4-HYDROXY-3-(MORPHOLINOMETHYL)BENZOIC ACID HYDRATE,4-hydroxy-3-(morpholinomethyl)benzoic acid hydrat
• 3-(Morpholinomethyl)benzoic acid (4,5-dihydro-4-oxo-1H-pyrazolo[3,4-d]pyrimidine-1-yl)methyl ester
• 4-(Morpholinomethyl)benzoic acid (4,5-dihydro-4-oxo-1H-pyrazolo[3,4-d]pyrimidine-1-yl)methyl ester
• 4-[2-[(4-Amino-5-chloro-2-ethoxybenzoylamino)methyl]morpholinomethyl]benzoic acid
• 4-(Morpholinomethyl)benzoic acid 4-(acetylamino)phenyl ester
• 4-[2-[(4-Amino-5-chloro-2-methoxybenzoylamino)methyl]morpholinomethyl]benzoic acid
• Bis[4-[morpholinomethyl]benzoic acid]2-[[[(2-amino-1,6-dihydro-6-oxo-9H-purin)-9-yl]methyl]oxy]-1,3-propanediyl ester
• 2-(Morpholinomethyl)benzoic acid 4-(acetylamino)phenyl ester
• 4-[2-[(4-Amino-5-chloro-2-ethoxybenzoylamino)methyl]morpholinomethyl]benzoic acid methyl ester
• POTASSIUM 4-(MORPHOLIN-4-YLMETHYL)BENZOATE
• methyl 4-(morpholin-4-ylmethyl)benzoate
• AKOS BB-9493
• 4-[(2-methylmorpholin-4-yl)methyl]benzoic acid