Hydrochloric Acid → (E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]aniline

HRID 976125Notes

Reaction equation

HRID 976125 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]([C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 570097054-[3-(1-Benzylpiperidin-4-yl)propenoyl]nitrobenzene

Product 1

HCID 19968908(E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]aniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.27 g of 4-[3-(1-benzylpiperidin-4-yl)propenoyl]-nitrobenzene was added to a mixed solution of 10 ml of acetic acid and 2 ml of hydrochloric acid, and then 1.38 g of stannous chloride was added thereto under ice cooling. The mixture was stirred for 24 hours while further adding 0.69 g of stannous chloride twice during the reaction. The solvent was removed under reduced pressure to obtain a crude product of (E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]aniline. Then, this was dissolved in 15 ml of ethanol, and to the solution was added 0.67 g of 4-chloro-5,6-dimethylpyrimidine. Subsequently, the mixture was reacted by heating at 60° C. for 30 minutes. The reaction mixture was neutralized by adding a 28% sodium methylate-methanol solution under cooling, solids were removed by filtration, and then the filtrate was consensed under reduced pressure. The obtained residue was applied to silica gel column chromatography to obtain 1.02 g of the title compound as pale yellow powder.

Workup

  1. customtwice during the reaction
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cbccf30b9419449380fa94a0ea80d186
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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