Trifluoroacetic acid → 4-[(1-Benzyl-4-piperidinyliden)acetyl]aniline

HRID 976151Notes

Reaction equation

HRID 976151 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:30])[CH:16]=[C:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:11][CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C[O-].[Na+].CO>C(Cl)(Cl)Cl>[CH2:23]([N:20]1[CH2:21][CH2:22][C:17](=[CH:16][C:15]([C:12]2[CH:11]=[CH:10][C:9]([NH2:8])=[CH:14][CH:13]=2)=[O:30])[CH2:18][CH2:19]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 19968896N-t-butoxycarbonyl-4-[(1-benzyl-4-piperidinyliden)acetyl]anilineHCID 23694274Sodium methanolate methanol

Product 1

HCID 199689364-[(1-Benzyl-4-piperidinyliden)acetyl]anilineYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4.12 g of N-t-butoxycarbonyl-4-[(1-benzyl-4-piperidinyliden)acetyl]aniline was added to 50 ml of chloroform, and then 10 ml of trifluoroacetic acid was added thereto. The mixture was stirred at room temperature for 4 hours. After the reaction, the reaction mixture was condensed under reduced pressure, and the residue was dissolved in chloroform. Then, the solution was neutralized by adding a 28% sodium methylate·methanol solution thereto. The residue obtained by condensation under reduced pressure was applied to silica gel column chromatography to obtain 2.33 g of the title compound as bluish green powder.

Workup

  1. customAfter the reaction
  2. customcondensed under reduced pressure
  3. customThe residue obtained by condensation under reduced pressure

Sources & evidence

ORD record
ord-dba69cfb462f4624832458f705ffa6ef
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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