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

HRID 976140Notes

Reaction equation

HRID 976140 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 70279862(E)-4-[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 (E)-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. During the reaction, 0.69 g of stannous chloride was further added twice. After completion of the reaction, the reaction mixture was condensed under reduced pressure to obtain 5.50 g of a crude product of the title compound. This was used without purification for the next reaction.

Workup

  1. additionwas further added twice
  2. customAfter completion of the reaction
  3. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-f358fc38bacd4c36af71ca2eff7151e2
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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