4-(Phenylmethyl)-2-morpholinemethanol

Green Oil

Synthesis of (4-benzylmorpholin-2-yl)methanol 20.3 g of 4-benzyl-2-chloromethylmorpholine, previously obtained, 3.5 ml of water and then 45 ml of formamide (75-12-7) are placed in a 250 ml round-bottomed flask with a condenser and a thermometer and under argon. The reaction medium is heated at 215° C. at the reflux of formamide for 3 h and then cooled to 50° C. with a bath of ice-cold water. A further 3.5 ml of water are added and the refluxing is resumed for a further 2 h. After returning to ambient temperature (20° C.), the medium is poured into ice-cold water (150 ml), the resulting mixture is basified with 10M sodium hydroxide (50 ml) at pH=12, extraction is carried out twice with toluene, and the organic phases are combined and washed with a saturated NaCl solution (50 ml), dried over magnesium sulfate and brought to dryness under a vacuum of 3 mbar for 1 h. (4-Benzylmorpholin-2-yl)methanol (13.4 g) is isolated in the form of an amber oil (yield=72percent).Step 3b: Synthesis of (4-benzylmorpholin-2-yl)methanol 20.3 g of 4-benzyl-2-chloromethylmorpholine, previously obtained, 3.5 ml of water and then 45 ml of formamide (75-12-7) are placed in a 250 ml round-bottomed flask with a condenser and a thermometer and under argon. The reaction medium is heated at 215° C. at the reflux of formamide for 3 h and then cooled to 50° C. with a bath of ice-cold water. A further 3.5 ml of water are added and the refluxing is resumed for a further 2 h. After returning to ambient temperature (20° C.), the medium is poured into ice-cold water (150 ml), the resulting mixture is basified with 10M sodium hydroxide (50 ml) at pH=12, extraction is carried out twice with toluene, and the organic phases are combined and washed with a saturated NaCl solution (50 ml), dried over magnesium sulfate and brought to dryness under a vacuum of 3 mbar for 1 h. (4-Benzylmorpholin-2-yl)methanol (13.4 g) is isolated in the form of an amber oil (yield=72percent).

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

Molecular Weight:207.27
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:207.125928785
Monoisotopic Mass:207.125928785
Topological Polar Surface Area:32.7
Heavy Atom Count:15
Complexity:181
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes