Hydrochloric Acid → HCID 13799019, compound

HRID 280153Notes

Reaction equation

HRID 280153 reaction equation
Cl[CH:2]1[C:10]2[C:5](=[C:6]([O:11][CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.Cl>C(Cl)(Cl)Cl>[CH3:12][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][CH:2]2[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 13799018HCID 13799018, compound

Product 1

HCID 13799019HCID 13799019, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1-chloro-4-methoxyindan (from Step 3) in chloroform (130 ml) is added over a period of ten minutes to a stirred mixture of piperidine (284 ml) in chloroform (400 ml) under nitrogen. The reaction mixture is heated to reflux for six hours and allowed to stand at RT overnight. The mixture is treated with 10% aqueous HCl and the organic layer separated. The aqueous layer is extracted with methylene chloride and the combined organic extracts washed with 10% aqueous HCl. The organic layer is evaporated in vacuo and the residue partitioned between 5% aqueous HCl and ether. The combined aqueous fraction is washed with ether, made alkaline, and the alkaline layer extracted with ether. The ether extract is washed, dried and concentrated in vacuo yielding the piperidine indan as an oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for six hours
  3. customthe organic layer separated
  4. extractionThe aqueous layer is extracted with methylene chloride
  5. washthe combined organic extracts washed with 10% aqueous HCl
  6. customThe organic layer is evaporated in vacuo
  7. customthe residue partitioned between 5% aqueous HCl and ether
  8. washThe combined aqueous fraction is washed with ether
  9. extractionthe alkaline layer extracted with ether
  10. extractionThe ether extract
  11. washis washed
  12. customdried
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9dda10ab0ae64d6892e7fd3f77ad158d
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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