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

HRID 417853Notes

Reaction equation

HRID 417853 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) game 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) game the title compound as a colorless oil

Sources & evidence

ORD record
ord-967a14a2464f4a9599f94f0c6669c5e3
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

Loading…