Morpholine → HCID 1268044, compound

HRID 339770Notes

Reaction equation

HRID 339770 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 6973630(-)-Glycidol

Product 1

HCID 1268044HCID 1268044, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-glycidol (1.00 mL, 15.0 mmol) and morpholine (1.96 mL, 22.5 mmol, 2.5 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 (2R)-3-(4-morpholinyl)-1,2-propanediol (2.47 g, 102%): 1H NMR (CDCl3) δ 2.37 (dd J=4.0, 12.4 Hz, 1H), 2.40-2.48 (m, 2H), 2.57 (dd, J=9.6, 12.4 Hz, 1H), 2.62-2.71 (m, 2H), 3.50 (dd, J=4.2, 11.4 Hz, 1H), 3.65-3.79 (m, 5H), 3.79-3.88 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-0d5c7a1ab3be495dbfeaa4f06723927e
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

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