Hydrochloric Acid → (E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-2-(4-hydroxyphenyl)-3-phenylpent-2-enamide

HRID 884053Notes

Reaction equation

HRID 884053 reaction equation
[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:34])/[C:14](/[C:24]2[CH:29]=[CH:28][C:27]([O:30]COC)=[CH:26][CH:25]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O.O>[CH3:35][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:34])/[C:14](/[C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57693048(E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enamide

Product 1

HCID 11373794(E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-2-(4-hydroxyphenyl)-3-phenylpent-2-enamideYield 91%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Method A; To a suspension of 4 (1.39 g, 2.93 mmol) in MeOH (4 ml) was added a solution of 3N HCl in AcOEt (10 ml) under ice cooling, and the mixture was stirred at room temperature for 2 h. A solution of NaHCO3 (2.8 g) in H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt and a little MeOH. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residual solid was triturated with Et2O to give 5 (91%). 5: colorless powder; 1H-NMR (CD3OD) δ 0.97 (3H, t, J=7.4 Hz), 2.38 (6H, s), 2.65 (2H, q, J=7.4 Hz), 2.82 (2H, t, J=5.4 Hz), 4.11 (2H, t, J=5.74 Hz), 6.50 (2H, d, J=8.8 Hz), 6.92 (2H, d, J=8.8 Hz), 6.94 (2H, d, J=9.2 Hz) 7.11-7.25 (5H, m), 7.53 (2H, d, J=9.1 Hz). 13C-NMR (CD3OD) δ 13.21, 30.40, 45.76, 59.09, 66.74, 115.69, 115.75, 123.42, 127.91, 129.10, 129.31, 130.42, 131 0.78,

Workup

  1. extractionthe whole was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residual solid was triturated with Et2O

Sources & evidence

ORD record
ord-85c705bc7ece4611a81e8085027c4e1f
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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