Morpholine → 4-(Pent-4-YN-1-YL)morpholine

HRID 1984081Notes

Reaction equation

HRID 1984081 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

HCID 8083MorpholineHCID 110197205-Iodo-1-pentyne

Product 1

HCID 234379134-(Pent-4-YN-1-YL)morpholine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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

  1. filtrationfiltered
  2. extractionthe mother liquor was extracted with 3N HCl
  3. extractionback-extracted into EtOAc
  4. customDrying
  5. concentration(Na2SO4), and concentration

Sources & evidence

ORD record
ord-b7853e5453874b828457949e84ebbcb7
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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