Morpholine → HCID 53264228, compound

HRID 1452759Notes

Reaction equation

HRID 1452759 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1.CCN(CC)CC.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>ClCCl>[CH2:11]([O:10][C:8]([C:6]1[O:7][C:3]([CH2:2][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:4][CH:5]=1)=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

Product 1

HCID 53264228HCID 53264228, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl 5-(chloromethyl)-2-furan-carboxylate (0.5 mL, 3.25 mmol) and Et3N (0.9 mL, 6.5 mmol) in dichloromethane under nitrogen was added morpholine (284 μL, 3.25 mmol) dropwise and a catalytic amount of KI. The reaction mixture was stirred at 45° C. for 24 hours, then it was concentrated in vacuo. The residue was dissolved in EtOAc and the organic layer was washed with water (2×) then brine, dried over sodium sulfate, filtered, concentrated, and dried in vacuo to give 520 mg (67% yield) of 5-morpholin-4-ylmethyl-furan-2-carboxylic acid ethyl ester as a light brown oil. 1H-NMR (d6-DMSO) δ: 7.22 (d, 1H), 6.51 (d, 1H), 4.25 (q, 2H), 3.54 (m, 6H), 2.37 (broad s, 4H), 1.27 (t, 3H).

Workup

  1. concentrationit was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe organic layer was washed with water (2×)
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6436a97be6144fa2b33db3e706403ec5
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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