Morpholine → 4-(3-Butyn-1-yl)morpholine

HRID 1984080Notes

Reaction equation

HRID 1984080 reaction equation
[CH2:1](OS(C)(=O)=O)[CH2:2][C:3]#[CH:4].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>CCOCC>[CH2:1]([N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH2:2][C:3]#[CH:4]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 11378578But-3-yn-1-yl methanesulfonate

Product 1

HCID 107730544-(3-Butyn-1-yl)morpholine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methanesulfonic acid but-3-ynyl ester (10.1 g, 68 mmol) and morpholine (12.5 mL, 143 mmol) was heated to 100° C. for 1 h. The mixture was diluted with Et2O (50 mL) and filtered. The solid residue was discarded, and the mother liquor extracted with 3N HCl. The aqueous layer was basified with NaOH, and back-extracted into EtOAc. Drying (Na2SO4), concentration, and distillation (short-path, b.p.=130° C. at ˜5 mm Hg) gave the title compound as a colorless oil. 1H NMR (CDCl3) δ 3.72 (t, 4H), 2.60 (t, 2H), 2.48 (t, 4H), 2.39 (td, 2H), 2.00 (t, 1H).

Workup

  1. filtrationfiltered
  2. extractionthe mother liquor extracted with 3N HCl
  3. extractionback-extracted into EtOAc
  4. customDrying
  5. concentration(Na2SO4), concentration, and distillation (short-path, b.p.=130° C. at ˜5 mm Hg)

Sources & evidence

ORD record
ord-da27fac848e640bf84cbb2303b967525
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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