ChemicalBook CAS DataBase List N-(2-HYDROXYPROPYL)MORPHOLINE

N-(2-HYDROXYPROPYL)MORPHOLINE synthesis

4synthesis methods

Product Name:N-(2-HYDROXYPROPYL)MORPHOLINE
CAS Number:2109-66-2
Molecular formula:C7H15NO2
Molecular Weight:145.2

6704-35-4
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2109-66-2
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Yield:-

Reaction Conditions:

with methanol;sodium tetrahydroborate at 0 - 20; for 12 h;

Steps:

6.1 1-morpholinopropan-2-ol
1-morpholinopropan-2-ol (0630) [284] To a solution of l-morpholinopropan-2-one (0.4 g, 2.79 mmol) in MeOH (5 mL) at 0 °C was added NaBH₄ (0.159 g, 4.19 mmol). The resulting reaction mixture was stirred at room temperature for 12 h. Progress of the reaction was monitored by TLC. After TLC indicated the reaction was complete, the reaction mixture was concentrated to dryness under reduced pressure. The residue was diluted with water and extracted with DCM. The combined organic layer was dried over anhydrous Na₂S0₄, filtered, and concentrated to get a crude residue. The crude compound was purified by silica gel column chromatography eluting with 0-5% MeOH/DCM to afford the title compound as a yellow oil (0.18 g, yield 43.8%). 1H NMR (400 MHz, DMSO-d6) δ 4.26 (d, = 4.4 Hz, 1H), 3.78 - 3.72 (m, 1H), 3.55 (t, =4.8 Hz, 4H), 2.37 (t, =4.0 Hz, 4H), 2.25 - 2.11 (m, 2H), 1.02 (d, = 6.0 Hz, 3H).

References:

SYROS PHARMACEUTICALS, INC.;ROBERTS, Christopher;ZHANG, Yi;BEAUMIER, Francis;LEPISSIER, Luce;MARINEAU, Jason, J.;RAHL, Peter, B.;SPROTT, Kevin;CIBLAT, Stephen;SOW, Boubacar;LAROUCHE-GAUTHER, Robin;BERSTLER, Lauren WO2016/196910, 2016, A1 Location in patent:Paragraph 283; 284

110-91-8 Synthesis