4-(4-NITROBENZYL)MORPHOLINE

yellow-orange to orange crystalline powder

PREPARATION 2: To a reaction flask was added p-nitrobenzyl bromide (72.084 g). A solution of 4-nitrobenzylbromide (4.30g, 20mmol)Dissolved in 40 ml of acetonitrile solvent, Then K2CO3 (5.52 g, 40 mmol) was added, KI (0.33 g, 2 mmol), Then, morpholine (1.91 g, 22 mmol) was added thereto, After 5 h, the reaction was complete.The reaction solution was concentrated and dried, And further adding 100 ml of H2O thereto, Extracted with ethyl acetate (150 ml x 3)The organic layer was collected and concentrated to give 4.17 g of a solid, 94percent yield.General procedure: 4-Nitrobenzyl bromide (10.8 g, 0.05 mol) or 4-chloronitrobenzene (7.9 g, 0.05 mol) was dissolved in acetonitrile (50 mL), excessive secondary amine (50 mL) was added, the reaction was stirred at room temperature for 3 h, water (100 mL) was added, and extracted two times with DCM. The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated to obtain the compounds 5a–e.General procedure: To the solution of 4-nitrobenzylbromide (10.8 g, 0.05mol) or 4-chloronitrobenzene (7.9 g, 0.05 mol) in acetonitrile(50 mL), excessive secondary amine (50 mL) was added andstirred at room temperature for 3 h. Then water (100 mL)was added and extracted two times with dichloromethane(CH2Cl2). The organic extracts were combined, dried oversodium sulfate, filtered, and concentrated to obtain the compounds5 and 7a-c.To a mixture of 1-bromomethyl-4-nitro-benzene (5.0 g, 29.1 mmol) and potassium carbonate (12.0 g, 87 mmol) in THF (100 mL) was added morpholine (6.35 mL, 73 mmol) in a slow stream. The reaction was stirred 24h at room temperature, was filtered through Celite and evaporated. Purification by flash chromatography (SiO2) provided 4-(4-nitro-benzyl)-morpholine (5.27 g, 81 percent yield) as a pale yellow solid. . 1H-NMR (DMSO-d6, 500 MHz) 8.20 (d, 2H), 7.60 (d, 2H), 3.61 (m, 6H), 2.38 (m, 4H) ppm; MS (FIA) 223.1 (M+H); HPLC (Method A) 1.577 min.General procedure: KOH (2.4mmol), HGeneral procedure: Under a NA solution of 20.0 g of morpholine in 600 ml chloroform is successively treated with 40.0 g of p-nitrobenzylchloride and 24.0 g of sodium carbonate at 65 °C for 18 h. Usual work-up and purification by column chromatography (eluent: hexane - ethyl acetate (8 - 10)) gives 40.4 g of compound 16.

Molecular Weight:222.24
XLogP3:1.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:222.10044231
Monoisotopic Mass:222.10044231
Topological Polar Surface Area:58.3
Heavy Atom Count:16
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes