Morpholine → HCID 86653793, compound

HRID 85125Notes

Reaction equation

HRID 85125 reaction equation
[F:1][CH:2]([F:12])[C:3]1[CH:10]=[C:9](F)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[F:1][CH:2]([F:12])[C:3]1[CH:10]=[C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 866522552-(Difluoromethyl)-4-fluorobenzaldehyde

Product 1

HCID 86653793HCID 86653793, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture containing 2-(difluoromethyl)-4-fluorobenzaldehyde (47; 3.50 g, 20.1 mmol), morpholine (48; 1.9 g, 22.1 mmol) and K2CO3 (5.5 g, 40.2 mmol) in 50 mL of DMSO was stirred at 100° C. for 4 h. The resulting reaction mixture was cooled to room temperature and diluted with water (200 mL). The precipitated solids were collected by filtration and dried to afford 2-(difluoromethyl)-4-morpholinobenzaldehyde 49 (2.5 g, 52%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to room temperature
  3. filtrationThe precipitated solids were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-127248687d564796a7bd1e3a9f48197d
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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