Toluene → 8-Azabicyclo[3.2.1]octane hydrochloride

HRID 1293147Notes

Reaction equation

HRID 1293147 reaction equation
[C@@H:1]12[N:8](C)[C@@H:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[Cl:10]C(OC(Cl)C)=O.C1(C)C=CC=CC=1>CO>[ClH:10].[CH:5]12[NH:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 5213051-Chloroethyl chloroformateHCID 637986Tropane

Product 1

HCID 5222728-Azabicyclo[3.2.1]octane hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tropane (900 mg), 1-chloroethyl chloroformate (1 ml), and toluene (20 ml) was heated and refluxed for 6 hours. After that, methanol (10 ml) was added to the reaction solution, and further refluxed for 4 hours. The solvent was distilled to yield the title compound (850 mg).

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 6 hours
  3. temperaturefurther refluxed for 4 hours
  4. distillationThe solvent was distilled

Sources & evidence

ORD record
ord-fe22afe8ae504626af06b4ebceeec28c
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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