Morpholine → HCID 89813599, compound

HRID 2172284Notes

Reaction equation

HRID 2172284 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1F.O1CCOCC1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C(Cl)Cl.CN(C=O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 1424144-Bromo-3-fluorobenzotrifluoride

Product 1

HCID 89813599HCID 89813599, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vial charged with potassium phosphate (0.533 g, 2.51 mmol), 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (0.610 g, 2.51 mmol) and 1 mL dioxane, was treated with morpholine (0.437 ml, 5.02 mmol) and was heated to 150° C. in a microwave reactor for one hour. LC/MS showed mostly starting material, so the reaction mixture was treated with 1 mL DMF and was heated to 150° C. in an oil bath overnight. LC/MS showed product, so the reaction mixture was diluted with DCM, filtered through a syringe filter, and concentrated. Purification of the resulting residue by silica gel column chromatography (0 to 50% EtOAc/heptane) gave 4-(2-bromo-5-(trifluoromethyl)phenyl)morpholine (0.280 g, 0.903 mmol) as a clear oil. [M+H]+=312.0

Workup

  1. temperaturewas heated to 150° C. in an oil bath overnight
  2. filtrationfiltered through a syringe
  3. filtrationfilter
  4. concentrationconcentrated
  5. customPurification of the resulting residue by silica gel column chromatography (0 to 50% EtOAc/heptane)

Sources & evidence

ORD record
ord-8836d701547545d09b8dcd4542e9f5a6
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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