p-Toluenesulfonic acid → 115661-42-2

HRID 266697Notes

Reaction equation

HRID 266697 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[Cl:23])[NH2:19].CC1C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:19][C:18]2[CH:20]=[CH:21][C:22]([Cl:23])=[C:16]([Cl:15])[CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 72573,4-DichloroanilineHCID 192201-Benzyl-4-piperidoneHCID 4311764Sodium borohydride

Product 1

HCID 10854237115661-42-2

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

190 mmol of 1-benzyl-4-piperidone, 240 mmol of 3,4-dichloroaniline, 0.02 g of PTSA and 200 ml of toluene are placed in a round-bottomed flask equipped with a reflux condenser and a Dean and Stark apparatus. The whole mixture is brought to reflux for 24 hours. After evaporation of the solvent, the residue is taken up in 500 ml of methanol and 450 mmol of sodium borohydride are progressively added. The whole mixture is kept stirring for two days. The expected product is obtained after concentration by filtration of the precipitate formed.

Workup

  1. customequipped with a reflux condenser
  2. temperatureto reflux for 24 hours
  3. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-3929200658124e9a870abb2589dd35f0
Source dataset
uspto-grants-1997_07
Patent number
US05652246

Reaction notes

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