تفاعل #635023

معادلة التفاعل

4-Bromomethylbenzophenone

4-bromomethyl benzophenone

2-(N-Ethylanilino)ethanol

NaH

→

desired product ( XIV )

المردود 80.0%

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

المردود 80.0%

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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 (IX) (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 (XIV) 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%); υmax (film/cm−1 1658 (s), 1598 (s), 1506 (s); δH (200 MHz; CDCl3) 1.22 (3H, t, J7, CH3), 3.49 (2H, q, J7, CH2CH3), 3.58-3.79 (4 H, m, OCH2CH2N), 4.66 (2H, s, ArCH2O), 6.69-6.79 (3H, m, ArH o- and p- to NR2), 7.28 (2H, dd, J7, 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 (40 ArCC═O), 143.2 (40 ArCCH2O), 147.7 (40 ArCNR2), 196.4 (C═O); n/z (APCI+) 360 ([M+H]+, 30%); HRMS C24H26O2N requires 360.1963; found 360.1963.

المصدر