Morpholine → HCID 58278897, compound

HRID 85108Notes

Reaction equation

HRID 85108 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:11][CH3:12])[O:9][CH3:10])=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.CC([O-])(C)C.[K+].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:10][O:9][CH:8]([O:11][CH3:12])[C:5]1[CH:6]=[CH:7][C:2]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:3][C:4]=1[C:13]([F:16])([F:15])[F:14]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 23665647Potassium tert-butoxideHCID 582793414-Chloro-1-(dimethoxymethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 58278897HCID 58278897, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-1-(dimethoxymethyl)-2-(trifluoromethyl)benzene (18; 3.20 g, 12.6 mmol), Pd2(dba)3 (0.30 g, 0.33 mmol), t-BuOK (3.50 g, 31.2 mmol) and morpholine (48; 1.09 g, 12.6 mmol) in anhydrous toluene (50 mL) was stirred under reflux for 12 h under an inert atmosphere of nitrogen. Upon cooling to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1) to give 4-(4-(dimethoxymethyl)-3-(trifluoromethyl)phenyl)morpholine 19 (0.40 g, 10.4%).

Workup

  1. temperatureunder reflux for 12 h under an inert atmosphere of nitrogen
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-07cd9b03c3f24d31af635aed082d9572
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

Loading…