Water → 4-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenyl [1,4']bipiperidinyl-1'-carboxylate

HRID 2222322Notes

Reaction equation

HRID 2222322 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N:22]1([CH:28]2[CH2:33][CH2:32][N:31]([C:34](Cl)=[O:35])[CH2:30][CH2:29]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.O>N1C=CC=CC=1>[N:22]1([CH:28]2[CH2:33][CH2:32][N:31]([C:34]([O:21][C:18]3[CH:17]=[CH:16][C:15](/[CH:14]=[C:11](\[C:12]#[N:13])/[C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)=[CH:20][CH:19]=3)=[O:35])[CH2:30][CH2:29]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 98133754-Piperidinopiperidine-1-carbonyl chlorideHCID 10446442(Z)-2-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)acrylonitrile2×

Product 1

HCID 866054194-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenyl [1,4']bipiperidinyl-1'-carboxylateYield 80.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Z)-2-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)acrylonitrile (compound 1) (0.28 g) and 4-piperidinopiperidinocarbonyl chloride (0.23 g) were dissolved in pyridine (5 ml), and the resultant solution was stirred for a whole day and night. After completion of reaction, the resultant reaction mixture was added to water (200 ml), and the thus-precipitated product was purified by means of silica gel chromatography employing a chloroform/methanol system, to thereby produce the target product (0.38 g, yield: 79%).

Workup

  1. customAfter completion of reaction
  2. customthe resultant reaction mixture
  3. customthe thus-precipitated product was purified by means of silica gel chromatography

Sources & evidence

ORD record
ord-fd4caf7db37e4510a05d11a393b338e4
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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