Reaction #1101965

Reaction equation

4-chloroacetophenone

morpholine

NaOt-Bu

CHCl3

→

52b

Yield 74.1%

N-(4-Acetylphenyl)morpholine

Yield 74.1%

Solvents

PhMe

Conditions

Workup

1. 1
   Temperaturecooled
2. 2
   Filtrationfiltered
3. 3
   OtherEvaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (83:2:15 to 78:2:20 hexane/Et3N/EtOAc, silica gel)

Procedure

According to General Procedure B, a mixture of 4-chloroacetophenone (65 μL, 0.50 mmol), morpholine (52 μL, 0.60 mmol), NaOt-Bu (67 mg, 0.70 mmol), Pd2(dba)3.CHCl3 (10 mg, 0.01 mmol) and 12f (8 mg, 0.02 mmol) in PhMe (2.5 mL) was heated, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (83:2:15 to 78:2:20 hexane/Et3N/EtOAc, silica gel) gave 52b (76 mg, 74%) as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.90 (d, 2H, J=9.0 Hz), 6.87 (d, 2H, J=9.0 Hz), 3.86 (t, 4H, J=4.8 Hz), 3.31 (t, 4H, J=5.1 Hz), 2.53 (s, 3H); 13C NMR (75.5 MHz, CDCl3) 196.4, 154.2, 130.3, 128.1, 113.2, 66.5, 47.5, 26.1.

Source