4-BENZYL-3-HYDROXYMETHYLMORPHOLINE

4-BENZYL-3-HYDROXYMETHYLMORPHOLINE Property

Boiling point:

322.7±22.0 °C(Predicted)

Density 

1.117±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.85±0.10(Predicted)

Appearance

Off-white to light yellow Solid-liquid mixture

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

4-BENZYL-3-HYDROXYMETHYLMORPHOLINE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of N-benzyl-3-hydroxymethylmorpholine from 4-benzyl-5-oxo-3-morpholinecarboxylic acid: triethylamine (7.29 g, 10.0 mL, 72 mmol) was added to a solution of intermediate 58 (17.7 g, 75.3 mmol) in tetrahydrofuran (THF, 300 mL). The reaction system was cooled to 0 °C and the borane dimethyl sulfide complex (~10 M solution of THF, 45 mL, 450 mmol) was slowly added. Subsequently, the reaction mixture was heated to reflux for 16 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and the excess borane was carefully destroyed. The excess THF was evaporated under reduced pressure and the residue was adjusted to strong basicity with 2 M NaOH solution (250 mL) and subsequently extracted with ethyl acetate (EtOAc, 3 x 150 mL). The aqueous phase was acidified to pH 1 with concentrated hydrochloric acid and extracted again. The combined organic phases were washed with brine (150 mL), dried over anhydrous magnesium sulfate (MgSO4), and concentrated under reduced pressure to give N-benzyl-3-hydroxymethylmorpholine (13.5 g, 87% yield) as a clear oil.1H NMR (CDCl3) δ: 7.29-7.16 (5H, m), 4.05 (1H, d, J = 12.8 Hz), 3.88 (1H dd, J = 11.5, 4.5 Hz), 3.78 (1H, m), 3.70-3.53 (2H, m), 3.51-3.40 (2H, m), 3.20 (1H, d, J = 13.2 Hz), 2.68 (1H, dt, J = 12.1, 2.8 Hz), 2.48 (1H, m), 2.27 (1H, m). 2.20-2.15 (1H, bs).

References

[1] Patent: WO2006/114606, 2006, A1. Location in patent: Page/Page column 58-59
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2577 - 2580