Benzene → 4,4-Diphenylpiperidine hydrochloride

HRID 1275222Notes

Reaction equation

HRID 1275222 reaction equation
[ClH:1].O.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[Al+3].[Cl-].[Cl-].[Cl-].O.[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[ClH:1].[C:15]1([C:6]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 2723901PiperonylamineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 30475044,4-Diphenylpiperidine hydrochlorideYield 72%

Procedure

A mixture of 4-piperidone monohydrate hydrochloride (15.0 g, 0.0976 mol) and AlCl3 (130 g, 0.976 mol, 10.0 eq) in anhydrous benzene (600 mL) were stirred at reflux for 4 hours. The mixture was cooled to room temperature, poured into ice (300 g) and water (50 mL), and filtered. The solid was washed with toluene and dried to afford 19.2 g (72%) of an off-white solid, which was characterized spectroscopically.

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationfiltered
  3. washThe solid was washed with toluene
  4. customdried

Sources & evidence

ORD record
ord-3fd39174c0b0405bb939ab3626c7b82e
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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