Morpholine → HCID 1268043, compound

HRID 339773Notes

Reaction equation

HRID 339773 reaction equation
[CH2:1]1[O:3][C@@H:2]1[CH2:4][OH:5].[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1>C(O)C>[N:6]1([CH2:1][C@H:2]([OH:3])[CH2:4][OH:5])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 5460455(+)-Glycidol

Product 1

HCID 1268043HCID 1268043, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (R)-glycidol (0.33 mL, 5.0 mmol) and morpholine (0.65 mL, 7.5 mmol, 1.5 equiv.) in abs. ethanol was heated in a microwave for 4 min. at 140 0° C., cooled to room temperature and concentrated at 70° C. under a 12 mBar vacuum to afford (2S)-3-(4-morpholinyl)-1,2-propanediol (0.91 g, 113%): 1H NMR (CDCl3) δ 2.37 (dd, J=3.9, 12.5 Hz, 1H), 2.41-2.48 (m, 2H), 2.57 (dd, J=9.7, 12.5 Hz, 1H), 3.51 (dd, J=4.3, 11.4 Hz, 1H), 3.66-3.79 (m, 5H), 3.81-3.87 (m, 1H).

Workup

  1. concentrationconcentrated at 70° C. under a 12 mBar vacuum

Sources & evidence

ORD record
ord-7f4186047c5c4bd996d988b3a920186d
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

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