Hydrogen Bromide → HCID 13711140, compound

HRID 255881Notes

Reaction equation

HRID 255881 reaction equation
Br.C[O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O.C>C(O)(=O)C.C(#N)C>[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 297Methane2×HCID 962WaterHCID 13799019HCID 13799019, compound

Product 1

HCID 13711140HCID 13711140, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent2×

Procedure

Hydrobromic acid (47-49%, 750 ml) is added to a stirred solution of the 4-methoxy-1-piperidinylindan (75 g) in glacial acetic acid (750 ml) under nitrogen. The mixture is refluxed for four hours, allowed to cool and poured into crushed ice and water. The pH of the ice mixture is adjusted to about 9 and the aqueous mixture extracted with methylene chloride. The methylene chloride extract is washed with water thereby forming a precipitate which is filtered and the solid dried. The methylene chloride layer is evaporated yielding an oil. The solid is dissolved in acetonitrile and treated with charcoal. The oil is treated with charcoal and dissolved in acetonitrile. Both dissolved materials are recrystallized from acetonitrile yielding the desired product, M.P. 134.5°-136.5° C.

Workup

  1. temperatureThe mixture is refluxed for four hours
  2. temperatureto cool
  3. additionpoured
  4. extractionthe aqueous mixture extracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. washis washed with water
  7. customthereby forming a precipitate which
  8. filtrationis filtered
  9. customthe solid dried
  10. customThe methylene chloride layer is evaporated
  11. customyielding an oil
  12. customBoth dissolved materials are recrystallized from acetonitrile yielding the desired product, M.P. 134.5°-136.5° C.

Sources & evidence

ORD record
ord-2d897fc3db42407bb525169b70759935
Source dataset
uspto-grants-1987_10
Patent number
US04699906

Reaction notes

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