Reaction #75451

Reaction equation

4-Bromomethylbenzophenone

2-(N-Ethylanilino)ethanol

NaH

→

desired product

Yield 80.0%

4-([N-Ethyl-N-phenyl-2-aminoethyl]oxymethyl)benzophenone

Yield 80.0%

Solvents

THF

Conditions

Workup

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 72 hours
3. 3
   OtherExcess solvent was removed in vacuo
4. 4
   workup.ADDITIONthe residue diluted with DCM
5. 5
   Washwashed with water and NaHCO3 solution (sat.)
6. 6
   Dryingdried (MgSO4) and solvent
7. 7
   Otherremoved under vacuum
8. 8
   OtherThe resulting oil was purified by flash chromatography
9. 9
   Washeluting with petroleum (bp 40-60° C.)

Procedure

2-(N-Ethylanilino)ethanol (3.03 g, 18.4 mmol, 1.2 eq) in THF (20 cm3) was treated with NaH (60% dispersion in oil, 524 mg, 13,1 mmol, 1.4 eq) and stirred at 20° C. for 1 hour. 4-Bromomethylbenzophenone (4.21 g, 15.3 mmol) was then added and stirring continued for 72 hours. Excess solvent was removed in vacuo and the residue diluted with DCM, washed with water and NaHCO3 solution (sat.), dried (MgSO4) and solvent removed under vacuum. The resulting oil was purified by flash chromatography, eluting with petroleum (bp 40-60° C.):EtOAc (9:1), to give the desired product as a yellow oil (4.36 g, 80%), Rf=0.54 (4:1, petrol:EtOAc) (Found: C, 78.34; H, 6.86; N, 5.29. C24H25NO2 requires C, 80.19; H, 7.01; N, 3.90%); νmax (film/cm−1 1658 (s), 1598 (s), 1506 (s); δH (200 MHz; CDCl3) 1.22 (3H, t, J 7, CH3), 3.49 (2H, q, J 7, CH2CH3), 3.58-3.79 (4H, m, OCH2CH2N), 4.66 (2H, s, ArCH2O), 6.69-6.79 (3H, m, ArH o- and p- to NR2), 7.28 (2H, dd, J 7, 7, ArH m- to NR2), 7.46-7.68 (5H, m, ArH), 7.80-7.88 (4H, m, ArH o- to C═O), δC (50.3 MHz; CDCl3) 12.2 (CH3), 45.5 (NCH2CH3), 50.1 (NCH2CH2O), 68.5 (NCH2CH2O), 72.2 (ArCH2O), 111.8 (ArCH o- to NR2), 115.8 (ArCH p- to NR2), 127.0, 128.3, 129.3, 130.0 and 130.3 (ArCH o- and m- to C═O and ArCH m- to NR2), 132.4 (ArCH p- to C═O), 136.8 and 137.7 (4° ArCC═O), 143.2 (4° ArCCH2O), 147.7 (4° ArCNR2), 196.4 (C═O); m/z (APCI+) 360 ([M+H]+, 30%); HRMS C24H26O2N requires 360.1963; found 360.1963.

Source