Morpholine → 4-(Pent-4-YN-1-YL)morpholine
Reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>CCOCC>[CH2:2]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)[CH2:3][CH2:4][C:5]#[CH:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 5-iodo-pent-1-yne (2.40 g, 12.3 mmol) and morpholine (2.70 g, 30.9 mmol) was heated to 80° C. for 15 min. The mixture was diluted with Et2O and filtered. The solid residue was discarded, and the mother liquor was extracted with 3N HCl. The aqueous layer was made basic with NaOH, and back-extracted into EtOAc. Drying (Na2SO4), and concentration gave the title compound as a pale orange oil. 1H NMR (CDCl3) δ 3.67 (t, 4H), 2.39 (m, 6H), 2.21 (td, 2H), 1.93 (t, 1H), 1.67 (quint., 2H).
Workup
- filtrationfiltered
- extractionthe mother liquor was extracted with 3N HCl
- extractionback-extracted into EtOAc
- customDrying
- concentration(Na2SO4), and concentration
Sources & evidence
- ORD record
- ord-49350dfb8b9f49b7a299651d1b1938b8
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093229B2
Reaction notes
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