Benzene → 4,4-Diphenylpiperidine hydrochloride

HRID 322108Notes

Reaction equation

HRID 322108 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, 97.6 mmol, 1.00 equiv) and AlCl3 (130 g, 976 mmol, 10.0 equiv) in anhydrous benzene (600 mL) was 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 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-390754aff24e448e9cbc944ebd0508e3
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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