Toluene → 1-Benzyl-5-(ethoxycarbonyl)-1-azoniabicyclo[3.3.1]nonane bromide

HRID 383936Notes

Reaction equation

HRID 383936 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]1CCC[Br:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(C)[CH:28]=CC=C[CH:24]=1>C(Cl)(Cl)Cl>[Br-:22].[CH2:1]([N+:8]12[CH2:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])([CH2:11][CH2:12][CH2:13]1)[CH2:28][CH2:23][CH2:24]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 68593821Ethyl 1-benzyl-(3-bromopropyl)piperidine-3-carboxylate

Product 1

HCID 198875961-Benzyl-5-(ethoxycarbonyl)-1-azoniabicyclo[3.3.1]nonane bromide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of ethyl 1-benzyl-(3-bromopropyl)piperidine-3-carboxylate (1.08 g), toluene (10 mL), and CHCl3 (2 mL) was heated under reflux for 2 hours. It was cooled to room temperature and then concentrated under reduced pressure. To the residue was added EtOAc, and the solid was collected by filtration to obtain 1-benzyl-5-(ethoxycarbonyl)-1-azoniabicyclo[3.3.1]nonane bromide (942 mg) as a colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added EtOAc
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-0ed8a905f4a64ca7a2fce9f150c22266
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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