Morpholine → HCID 66611279, compound

HRID 2204686Notes

Reaction equation

HRID 2204686 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]([Br:15])[C:12]([CH2:16]Br)=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=O)C.C(N(CC)CC)C.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CC(C)=O.C(OCC)(=O)C>[Br:15][C:13]1[C:12]([CH2:16][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([OH:4])[CH:14]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 66611712HCID 66611712, compound

Product 1

HCID 66611279HCID 66611279, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-(acetyloxy)-4-bromo-5-(bromomethyl)benzoate (may be prepared as described in Description 16; 741 mg, 2.03 mmol) in acetone (5 ml) was added triethylamine (0.56 ml, 4.05 mmol) and morpholine (0.23 ml, 2.63 mmol). The mixture was stirred for 1 hour, then the solvent was removed in vacuo to give a residue. The residue was redissolved in ethyl acetate (10 ml) and washed with water (10 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give oil. Purification by column chromatography (SiO2, 3:1-1:1 cyclohexane/ethyl acetate) gave the product as oil. 580 mg.

Workup

  1. customthe solvent was removed in vacuo
  2. customto give a residue
  3. washwashed with water (10 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give oil
  7. customPurification by column chromatography (SiO2, 3:1-1:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-f540361070ef43f4a0f449ca2dbd9a37
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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