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

HRID 1797276Notes

Reaction equation

HRID 1797276 reaction equation
[CH2:1]([N:3]([CH2:10][CH2:11][OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[H-].[Na+].Br[CH2:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1>C1COCC1>[CH2:1]([N:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:10][CH2:11][O:12][CH2:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 623382-(N-ethylanilino)ethanolHCID 1229514-(Bromomethyl)benzophenone

Product 1

HCID 221775034-([N-Ethyl-N-phenyl-2-aminoethyl]oxymethyl)benzophenoneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °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%); vmax (film/cm−1 1658 (s), 1598 (s), 1506 (s); δH (200 MHz; CDCl3) 1.22 (3 H, t, J 7, CH3), 3.49 (2 H, q, J 7, CH2CH3), 3.58–3.79 (4 H, m, OCH2CH2N), 4.66 (2 H, s, ArCH2O), 6.69–6.79 (3 H, m, ArH o- and p- to NR2), 7.28 (2 H, dd, J 7, 7, ARH m- to NR2), 7.46–7.68 (5 H, m, ArH), 7.80–7.88 (4 H, 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 (APCl+) 360 ([M+H]+, 30%); HRMS C24H26O2N requires 360.1963; found 360.1963.

Workup

  1. stirringstirring
  2. waitcontinued for 72 hours
  3. customExcess solvent was removed in vacuo
  4. additionthe residue diluted with DCM
  5. washwashed with water and NaHCO3 solution (sat.)
  6. dry with materialdried (MgSO4) and solvent
  7. customremoved under vacuum
  8. customThe resulting oil was purified by flash chromatography
  9. washeluting with petroleum (bp 40–60° C.)

Sources & evidence

ORD record
ord-e961231b26984dbaa088832b4b1977e6
Source dataset
uspto-grants-2006_04
Patent number
US07034129B2

Reaction notes

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