Reaction #59680

Reaction equation

triethylamine

3-(4-morpholinyl)benzenamine

Intermediate 3

3-(4-morpholinyl)benzenamine

3-Iodo4-methylbenzoyl chloride

Intermediate 1

3-Iodo4-methylbenzoyl chloride

→

desired product

Yield 67.5%

3-Iodo-4-methyl-N-[3-(4-morpholinyl)phenyl]benzamide

Yield 67.5%

Solvents

dimethyl formamide

Conditions

Workup

1. 1
   OtherThe solvent was removed in vacuo
2. 2
   WashThe organic layer was washed with water (2×100 ml), 2M sodium hydroxide solution (100 ml) and brine (100 ml)
3. 3
   Dryingdried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Othersolvent removed in vacuo
6. 6
   Filtrationcollected by filtration

Procedure

3-Iodo4-methylbenzoyl chloride (Intermediate 1) (19.5 g, 69.6 mmol) was added portion-wise to a mixture of triethylamine (48 ml, 350 mmol) and 3-(4-morpholinyl)benzenamine (Intermediate 3) (12.6 g, 70.6 mmol) in dimethyl formamide (150 ml) and the mixture was heated at 80° C. for 16 hours. The solvent was removed in vacuo and the residue taken up in chloroform (200 ml). The organic layer was washed with water (2×100 ml), 2M sodium hydroxide solution (100 ml) and brine (100 ml), dried over magnesium sulfate, filtered and solvent removed in vacuo. The resulting yellow solid was titurated with diethyl ether and collected by filtration to yield the desired product as an off-white solid (20.0 g, 47.0 mmol). The product was used in subsequent reactions without further purification.

Source