Water → (E)-N-[4-(3-hydroxypiperidinomethyl)phenyl]-3-(4-methylphenyl)cinnamamide

HRID 1277084Notes

Reaction equation

HRID 1277084 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:5][CH:4]=1.[OH:27][CH:28]1[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]1.O>CN(C=O)C>[OH:27][CH:28]1[CH2:33][CH2:32][CH2:31][N:30]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)[CH:14]=3)=[CH:5][CH:4]=2)[CH2:29]1

Participants

5

Reactant 3

HCID 962WaterHCID 232933-HydroxypiperidineHCID 18472214(E)-N-[4-(chloromethyl)phenyl]3-(4-methylphenyl)cinnamamide

Product 1

HCID 18472270(E)-N-[4-(3-hydroxypiperidinomethyl)phenyl]-3-(4-methylphenyl)cinnamamideYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (3 ml) was dissolved (E)-N-[4-(chloromethyl)phenyl]-3-(4-methylphenyl)cinnamamide (200 mg), and to the mixture was added 3-hydroxypiperidine(168 mg). The mixture was stirred at room temperature for 13 hours, and to the mixture was added water (50 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetatediisopropylether to give (E)-N-[4-(3-hydroxypiperidinomethyl)phenyl]-3-(4-methylphenyl)cinnamamide (Compound 67) (174 mg) as colorless crystals.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetatediisopropylether

Sources & evidence

ORD record
ord-53241307fb4b48dca48d4841a6d9e660
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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