Potassium Iodide → Methyl 2-(benzyloxy)-5-(morpholin-4-yl)benzoate

HRID 454508Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:10][CH2:11][O:12][CH2:13][CH2:14]Cl.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:21]([CH:26]=1)[C:22]([O:24][CH3:25])=[O:23]>C(OCC)(=O)C.O.CN(C)C(=O)C>[CH2:28]([O:27][C:20]1[CH:19]=[CH:18][C:17]([N:16]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (0.54 g), potassium iodide (0.11 g), and bis(2-chloroethyl)ether (0.22 mL) were sequentially added to an N,N-dimethylacetamide (3.2 mL) solution of methyl 5-amino-2-(benzyloxy)benzoate (0.40 g), followed by stirring at 100° C. for 3 hours. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 85-60% hexane/ethyl acetate] to obtain 0.27 g of methyl 2-(benzyloxy)-5-(morpholin-4-yl)benzoate as a light yellow oily substance.

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography [eluent: 85-60% hexane/ethyl acetate]

Sources & evidence

ORD record: ord-85dd3bddb98b49e18ad728a192720a65
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492582B2

Reaction notes

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