Hydrochloric Acid → 1-methyl-4-(8H-dibenzo[a,e]furo[3,4-c]cyclohepten-8-ylidene)-piperidine

HRID 1283318Notes

Reaction equation

HRID 1283318 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[CH:19]4[O:23][CH:22]([C:11]=3[C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)C=C4)[CH2:4][CH2:3]1.C1(C2C(=O)C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C=2C2C=CC=CC=2)C=CC=CC=1.Cl>C1(C)C(C)=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3=[CH:19][O:23][CH:22]=[C:11]3[C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 680682,3,4,5-Tetraphenyl-2,4-cyclopentadien-1-oneHCID 123688831-methyl-4-(1,4-dihydro-1,4-epoxy-9H-tribenzo[a,c,e]cyclohepten-9-ylidene)-piperidine

Product 1

HCID 123688861-methyl-4-(8H-dibenzo[a,e]furo[3,4-c]cyclohepten-8-ylidene)-piperidine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 3.20 g. (0.0093 mole) of 1-methyl-4-(1,4-dihydro-1,4-epoxy-9H-tribenzo[a,c,e]cyclohepten-9-ylidene)-piperidine in 105 ml. of xylene (b.p. 139°-140°) is added 3.60 g. (0.00936 mole) of tetraphenylcyclopentadienone ("tetracyclone"). The solution is stirred and refluxed for 22 hours. To the cooled solution is added 100 ml. of 3N hydrochloric acid. The crystalline solid that forms is removed by filtration and is washed thoroughly with benzene and ether. The white crystalline solid is dissolved in warm water and is treated with a solution of sodium carbonate. The resulting precipitate is extracted into benzene, washed with water, dried over magnesium sulfate, filtered, and the benzene is removed on a rotary evaporator. The crystalline residue, weighing 2.62 gm., is recrystallized from absolute methanol to give 1-methyl-4-(8H-dibenzo[a,e]furo[3,4-c]cyclohepten-8-ylidene)-piperidine, m.p. 147°-148°.

Workup

  1. temperaturerefluxed for 22 hours
  2. additionTo the cooled solution is added 100 ml
  3. customThe crystalline solid that forms is removed by filtration
  4. washis washed thoroughly with benzene and ether
  5. dissolutionThe white crystalline solid is dissolved in warm water
  6. additionis treated with a solution of sodium carbonate
  7. extractionThe resulting precipitate is extracted into benzene
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customthe benzene is removed on a rotary evaporator
  12. custom, is recrystallized from absolute methanol

Sources & evidence

ORD record
ord-ddffbc6260e448c9a1c604b52900127e
Source dataset
uspto-grants-1976_08
Patent number
US03974285

Reaction notes

Loading…