Methanol → 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl[1,4']bipiperidinyl-1'-carboxylate hydrochloride

HRID 2366411Notes

Reaction equation

HRID 2366411 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](O)[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].[Cl:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:32][CH2:31]1)=[O:29].C[OH:43]>N1C=CC=CC=1>[ClH:27].[C:12](/[C:11](/[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[CH:14]\[C:15]1[S:16][C:17]([N:20]2[CH2:25][CH2:24][CH:23]([CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][N:36]3[CH:33]3[CH2:34][CH2:35][N:30]([C:28]([OH:43])=[O:29])[CH2:31][CH2:32]3)[CH2:22][CH2:21]2)=[CH:18][CH:19]=1)#[N:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 98133754-Piperidinopiperidine-1-carbonyl chlorideHCID 16757522(Z)-2-(3,4-dimethoxyphenyl)-3-(5-(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrile

Product 1

HCID 672285281-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl[1,4']bipiperidinyl-1'-carboxylate hydrochlorideYield 30%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 6 (2.00 g) was dissolved in pyridine (50 mL), and 1-chlorocarbonyl-4-piperidinopiperidine (2.50 g) 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 under reduced pressure, 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: 974 mg, 30%).

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 under reduced pressure
  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-496751a46a364fe58662320598d58b09
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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