Sodium Iodide → 4-(Morpholin-4-yl)benzamide

HRID 56114

Reaction equation

HRID 56114 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:22][CH2:23][CH2:24]Cl)[CH2:20]Cl>CN(C=O)C.O>[O:22]1[CH2:23][CH2:24][N:1]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=2)[CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 760794-Aminobenzamide

Product 1

HCID 221422424-(Morpholin-4-yl)benzamideYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-aminobenzamide (6.81 g, 50 mmol) in DMF (70 mL) were added NaI (22.48 g, 150 mmol) and K2CO3 (13.82 g, 100 mmol). The mixture was heated to 140° C. and 2,2′-dichlorodiethyl ether (14.30 g, 100 mmol) was added. The reaction mixture was heated at 150° C. for 5 h, and cooled to rt. The mixture was diluted with water (100 mL), stirred for 10 min, and filtered. The filter cake was washed with water and dried to give the title compound as a yellow solid (6.60 g, 64%).

Workup

  1. temperatureThe reaction mixture was heated at 150° C. for 5 h
  2. temperaturecooled to rt
  3. filtrationfiltered
  4. washThe filter cake was washed with water
  5. customdried

Sources & evidence

ORD record
ord-c5a4edc26e8649629981307c9899858c
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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