Acetone → HCID 22288086, compound

HRID 968170Notes

Reaction equation

HRID 968170 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CC(C)=O.[Br:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1>C(OCC)(=O)C>[Br-:18].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N+:8]2([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 7721p-Xylyl bromideHCID 10130194HCID 10130194, compound

Product 1

HCID 22288086HCID 22288086, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A reaction container was charged with 1-(4-methylphenyl)piperidine (4.0 g, 22.8 mmol) and 10 ml of acetone and the mixture was stirred at ambient temperature. Then, α-bromo-p-xylene (5 g, 27.4 mmol) was added to the reaction solution. The reaction solution was stirred for 3 hours and 20 ml of ethyl acetate was added to the solution. The reaction mixture was further stirred for 30 minutes and subjected to suction filtration to collect a white powder. The resulting powder was dried to obtain 4-methylbenzyl(4-methylphenyl)piperidiniumbromide (6.8 g, yield: 83%).

Workup

  1. stirringThe reaction solution was stirred for 3 hours
  2. stirringThe reaction mixture was further stirred for 30 minutes
  3. filtrationsubjected to suction filtration
  4. customto collect a white powder
  5. customThe resulting powder was dried

Sources & evidence

ORD record
ord-881789662ee845d1b753f14e434c02a7
Source dataset
uspto-grants-2005_10
Patent number
US06958205B2

Reaction notes

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