Methanol → 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl diethyl-carbamate

HRID 2366441Notes

Reaction equation

HRID 2366441 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[S:16][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]3)=[CH:18][CH:19]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:27]([N:29]([CH2:33][CH3:34])[C:30](Cl)=[O:31])[CH3:28].CO>N1C=CC=CC=1>[CH2:27]([N:29]([CH2:33][CH3:34])[C:30](=[O:31])[O:26][CH:23]1[CH2:22][CH2:21][N:20]([C:17]2[S:16][C:15](/[CH:14]=[C:11](\[C:12]#[N:13])/[C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:19][CH:18]=2)[CH2:25][CH2:24]1)[CH3:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 6916Diethylcarbamoyl chlorideHCID 16757522(Z)-2-(3,4-dimethoxyphenyl)-3-(5-(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrile

Product 1

HCID 119647861-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl diethyl-carbamateYield 21.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 6 (150 mg) was dissolved in pyridine (1 mL), and diethylcarbamoyl chloride (55 mg) was added to the solution, followed by stirring under reflux for 2 hours. After completion of reaction, methanol was added to the reaction mixture, followed by stirring for 30 minutes. The solvent was evaporated to dryness, and the residue was extracted with chloroform and purified water. The organic layer was dried over sodium sulfate anhydrate, and the solvent was evaporated to dryness. The residue was recrystallized from ethyl acetate, to thereby yield the target product (yield: 40.6 mg, 21.3%).

Workup

  1. temperatureunder reflux for 2 hours
  2. additionwas added to the reaction mixture
  3. stirringby stirring for 30 minutes
  4. customThe solvent was evaporated to dryness
  5. extractionthe residue was extracted with chloroform
  6. custompurified water
  7. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  8. customthe solvent was evaporated to dryness
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b78371643ff24664b06ba5e8a400dc21
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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