p-Toluenesulfonic acid → HCID 18506983, compound

HRID 1992048Notes

Reaction equation

HRID 1992048 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([NH:16][C:17]1[C:18]([NH2:23])=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1(C)C=CC(S(O)(=O)=O)=C[CH:25]=1>C(OC(OCC)(OCC)C)C>[CH2:1]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([N:16]1[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:23]=[C:24]1[CH3:25])[CH2:10]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 21132356N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl)benzene-1,2-diamine

Product 1

HCID 18506983HCID 18506983, compound

Reagents, catalysts & solvents 1

HCID 66221Triethyl orthoacetateSolvent

Procedure

7.7 g (25.08 mmol) N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)benzene-1,2-diamine was refluxed in 200 ml of 1,1,1-triethoxyethane for 18 hrs. The mixture was cooled to ambient temperature and the solvent was then removed. The residue was dissolved in toluene and 1.8 g (9.47 mmol) of p-toluenesulfonic acid was added and the reaction mixture was heated to reflux while stirring for 18 hrs. The mixture was cooled to ambient temperature and filtered off solid and removed toluene under reduced pressure. The crude product was purified by flash column chromatography with 5% methanol and 0.5% ammonium hydroxide in dichloromethane on silica gel. 2.2 g of the product was recovered as a yellow residue.

Workup

  1. customthe solvent was then removed
  2. dissolutionThe residue was dissolved in toluene
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux
  5. temperatureThe mixture was cooled to ambient temperature
  6. filtrationfiltered off solid
  7. customremoved toluene under reduced pressure
  8. customThe crude product was purified by flash column chromatography with 5% methanol and 0.5% ammonium hydroxide in dichloromethane on silica gel
  9. custom2.2 g of the product was recovered as a yellow residue

Sources & evidence

ORD record
ord-e56f9eabb251422494e2df9c6bfdbd89
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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