(4-BENZYL-1,4-OXAZINAN-2-YL)METHANOL Chemical Properties

Boiling point:

114°C 0,05mm

Density 

1.117±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

pka

14.36±0.10(Predicted)

color 

Clear Pale Yellow

CAS DataBase Reference

40987-24-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

24/25-39-26

Hazard Note 

Irritant

HS Code 

2934999090

(4-BENZYL-1,4-OXAZINAN-2-YL)METHANOL Usage And Synthesis

Chemical Properties

Green Oil

Uses

Intermediate in the preparation of various antidepressants and protein kinase inhibitors.

Synthesis

Step 3b: Synthesis of (4-benzylmorpholin-2-yl)methanol 20.3 g of 4-benzyl-2-chloromethylmorpholine, 3.5 mL of water and 45 mL of formamide (CAS: 75-12-7) were added to a 250 mL round-bottom flask in a unit equipped with a condenser tube and a thermometer under argon protection. The reaction mixture was heated to 215 °C and reacted under formamide reflux conditions for 3 h, followed by cooling to 50 °C using an ice water bath. An additional 3.5 mL of water was added and the reaction was continued at reflux for 2 hours. After the reaction solution was cooled to room temperature (20 °C), it was poured into 150 mL of ice water and the pH was adjusted to 12 with 50 mL of 10 M sodium hydroxide solution for two extractions. The organic phases were combined, washed with 50 mL of saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and subsequently dried under vacuum at 3 mbar for 1 hour. A final 13.4 g of (4-benzylmorpholin-2-yl) methanol was obtained as an amber colored oil (72% yield).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2227 - 2244
[2] Patent: US2013/274253, 2013, A1. Location in patent: Paragraph 1825-1826
[3] Synthetic Communications, 1980, vol. 10, # 1, p. 59 - 74

(4-BENZYL-1,4-OXAZINAN-2-YL)METHANOL(40987-24-4)Related Product Information

• (4-BENZYL-1,4-OXAZINAN-2-YL)METHYLAMINE
• 4-Benzyl-2-(hydroxymethyl)homomorpholine
• 4-(4-METHOXY-BENZYL)-MORPHOLINE-2-CARBOXYLIC ACID HYDROCHLORIDE
• (S)-N-BENZYL-2-HYDROXYMETHYLMORPHOLINE
• 4-(3-CHLORO-BENZYL)-MORPHOLINE-2-CARBOXYLIC ACID HYDROCHLORIDE
• 4-BENZYL-2-MORPHOLINECARBOXYLIC ACID HYDROCHLORIDE
• 4-(4-CHLORO-BENZYL)-MORPHOLINE-2-CARBOXYLIC ACID HYDROCHLORIDE
• 4-(2-CHLORO-BENZYL)-MORPHOLINE-2-CARBOXYLIC ACID HYDROCHLORIDE
• 4-BENZYL-MORPHOLINE-2-CARBOXYLIC ACID
• 4-(3,4-DICHLORO-BENZYL)-MORPHOLINE-2-CARBOXYLIC ACID HYDROCHLORIDE
• (4-BENZYL-1,4-OXAZINAN-2-YL)METHANOL