Phenethylamine → Methyl 4-(phenylethylamino)crotonate

HRID 1938763Notes

Reaction equation

HRID 1938763 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].Br[CH2:16]/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20]>C1COCC1>[C:3]1([CH2:2][CH2:1][NH:9][CH2:16]/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 516892Sodium BicarbonateHCID 53691752-Butenoic acid, 4-bromo-, methyl ester

Product 1

HCID 23291030Methyl 4-(phenylethylamino)crotonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenethylamine (20 mL, 160 mmol) in anhydrous THF (250 mL) was added NaHCO3 (7 g) followed by methyl 4-bromocrotonate (10 mL, 84 mmol). After stirring for 4 h the reaction was concentrated to approximately half the volume and filtered through a pad of silica gel and eluted with 2% MeOH/CHCl3 to wash off the product. The crude product obtained after evaporation of the filtrate was purified by flash chromatography (silica gel, 2% MeOH/CHCl3) to give the title compound as a slightly yellow liquid (16.5 g, 81%). TLC Rf 0.53 (5% MeOH/CHCl3); 1H NMR (CDCl3) δ1.2 (1H, s), 2.8 (4H, br s), 3.35 (2H, dd), 3.7 (3H, s), 5.95 (1H, dt), 7.0 (1H, dt), 7.25 (5H, br s)

Workup

  1. concentrationwas concentrated to approximately half the volume
  2. filtrationfiltered through a pad of silica gel
  3. washeluted with 2% MeOH/CHCl3
  4. washto wash off the product
  5. customThe crude product obtained
  6. customafter evaporation of the filtrate
  7. customwas purified by flash chromatography (silica gel, 2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-e99aeea937974544a9032c9188880aff
Source dataset
uspto-grants-1997_12
Patent number
US05693636

Reaction notes

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