Morpholine → HCID 90020640, compound

HRID 2200186Notes

Reaction equation

HRID 2200186 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.CCN(C(C)C)C(C)C.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CN(C=O)C>[N+:12]([C:4]1[CH:3]=[C:2]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 70154111-Bromo-3-nitro-5-(trifluoromethyl)benzene

Product 1

HCID 90020640HCID 90020640, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 1-bromo-3-nitro-5-(trifluoromethyl)benzene (270 mg, 1 mmol) and DIEA (258 mg, 2 mmol) in DMF (5 mL), add morpholine (174 mg, 2 mmol). Stir the reaction at 120° C. overnight. Cool to room temperature; remove the volatiles under reduced pressure to give a crude residue. Purification of the residue by chromatography (silica gel, EtOAc:PE=1:5) affords the product (138 mg, 50%).

Workup

  1. customthe reaction at 120° C. overnight
  2. customremove the volatiles under reduced pressure
  3. customto give a crude residue
  4. customPurification of the residue by chromatography (silica gel, EtOAc:PE=1:5)

Sources & evidence

ORD record
ord-6787e43971da4c27836aeeb984848e1a
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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