Hydrochloric Acid → 4-(3-Bromo-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-piperidine

HRID 27089Notes

Reaction equation

HRID 27089 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2(O)[C:14]3[CH:15]=[C:16]([Br:19])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.Cl.Cl.CN1CCC(=C2C3C=C(Br)C=CC=3C=CC3C=CC=CC2=3)CC1>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([Br:19])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 134042481-methyl-4-(3-bromo-5-hydroxy-5H-dibenzo[a,d]cyclohepten-5-yl)piperidineHCID 23343662(+/-)-1-methyl-4-(3-bromo-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride

Product 1

HCID 233436594-(3-Bromo-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.86 g. (0.003 mol) of 1-methyl-4-(3-bromo-5-hydroxy-5H-dibenzo[a,d]cyclohepten-5-yl)piperidine in 30 ml. of trifluoroacetic acid and 15 ml. of trifluoroacetic anhydride is stirred and refluxed for 16 hours. The solvents are removed by evaporation on a rotary evaporator. The residue is dissolved in chloroform, and this chloroform solution is washed with sodium hydroxide solution, water, dried over magnesium sulfate, and filtered. Evaporation of the chloroform from the filtrate gives 0.88 g. of a yellow oil. This oil is dissolved in a minimum amount of absolute ethanol, treated with ethanolic HCl, and is cooled. The white crystalline material that precipitates is collected by filtration and is recrystallized from acetonitrile to give 0.67 g. of (±)-1-methyl-4-(3-bromo-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride.

Workup

  1. temperaturerefluxed for 16 hours
  2. customThe solvents are removed by evaporation on a rotary evaporator
  3. dissolutionThe residue is dissolved in chloroform
  4. washthis chloroform solution is washed with sodium hydroxide solution, water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customEvaporation of the chloroform from the filtrate
  8. customgives 0.88 g
  9. temperatureis cooled
  10. customThe white crystalline material that precipitates
  11. filtrationis collected by filtration
  12. customis recrystallized from acetonitrile
  13. customto give 0.67 g

Sources & evidence

ORD record
ord-a3d7858421f34a81ad9ce2a9bf8797d8
Source dataset
uspto-grants-1980_09
Patent number
US04220651

Reaction notes

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