Dimethylformamide → 6-{4-[2-(Benzyl-phenethyl-amino)-ethyl]-phenoxy}-nicotinamide

HRID 130689Notes

Reaction equation

HRID 130689 reaction equation
C(=O)(O)[O-].[Na+].[CH2:6]([NH:13][CH2:14][CH2:15][C:16]1[CH:31]=[CH:30][C:19]([O:20][C:21]2[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][N:22]=2)=[CH:18][CH:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CN(C=O)C>O>[CH2:6]([N:13]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:14][CH2:15][C:16]1[CH:31]=[CH:30][C:19]([O:20][C:21]2[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][N:22]=2)=[CH:18][CH:17]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7666Phenethyl bromideHCID 516892Sodium BicarbonateHCID 444340576-(4-(2-(Benzylamino)ethyl)phenoxy)nicotinamide

Product 1

HCID 597299896-{4-[2-(Benzyl-phenethyl-amino)-ethyl]-phenoxy}-nicotinamideYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add sodium bicarbonate (0.0823 g, 0.980 mmol) to a stirred solution of 6-[4-(2-benzylamino-ethyl)-phenoxy]-nicotinamide (0.3061 g, 0.881 mmol), (2-bromoethyl)benzene (0.135 mL, 0.988 mmol), and DMF (5 mL). Heat the reaction to reflux for 3 h under nitrogen and then cool to room temperature. Pour the reaction into water (50 mL) and extract with diethyl ether (3×50 mL). Dry the diethyl ether extracts over magnesium sulfate and then filter off the magnesium sulfate. Concentrate on a rotary evaporator and purify the crude product by flash chromatography on silica gel eluting with 90% ethyl acetate/hexanes to yield 0.1538 g (39%) of 6-{4-[2-(benzyl-phenethyl-amino)-ethyl]-phenoxy}-nicotinamide: mass spectrum (ion spray): m/z=452.1 (M+1); 1H NMR (CDCl3): 8.55 (d, 1H), 8.13 (dd, 1H), 7.29-7.11 (m, 14H), 7.01 (d, 2H), 6.92 (d, 1H), 3.71 (s, 1H), 2.94-2.77 (m, 9H).

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux for 3 h under nitrogen
  4. additionPour
  5. extractionextract with diethyl ether (3×50 mL)
  6. dry with materialDry the diethyl ether
  7. filtrationfilter off the magnesium sulfate
  8. concentrationConcentrate on a rotary evaporator
  9. custompurify the crude product by flash chromatography on silica gel eluting with 90% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6ae0ac51a1f54167ab666babe64fcff1
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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