Hydrochloric Acid → HCID 12368887, compound

HRID 442234Notes

Reaction equation

HRID 442234 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][C:22](C)([C:11]=3[C:10]3[CH:25]=[CH:26][CH:27]=[CH:28][C:9]2=3)[CH:21]=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][C:22]([CH3:21])=[C:11]3[C:10]3[CH:25]=[CH:26][CH:27]=[CH:28][C:9]2=3)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68068Tetraphenyl-2,4-cyclopentadien-1-oneHCID 123688851-methyl-4-(1-methyl-1,4-dihydro-1,4-epoxy-9H-tribenzo[a,c,e]cyclohepten-9-ylidene)piperidine

Product 1

HCID 12368887HCID 12368887, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 2.00 g. (0.00545 mole) of 1-methyl-4-(1-methyl-1,4-dihydro-1,4-epoxy-9H-tribenzo[a,c,e]cyclohepten-9-ylidene)piperidine and 2.16 g. (0.0056 mole) of tetraphenylcyclopentadienone in 60 ml. of xylene (b.p. 139°-140°) is stirred and refluxed for 20 hours. After cooling, 30 ml. of 6N hydrochloric acid is added. The precipitate that forms is removed by filtration and the solid precipitate is washed with ether and benzene. The solid is collected and made basic with 40% sodium hydroxide solution. The mixture is extracted with ether, and the ether extract is washed with water and dried over magnesium sulfate. After filtration, the ether is removed to give a crystalline residue which is recrystallized from methanol to give 1-methyl-4-(1-methyl-8H-dibenzo[a,e]furo[3,4-c]cyclohepten-8-ylidene)piperidine, m.p. 80°-86°.

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureAfter cooling
  3. customThe precipitate that forms is removed by filtration
  4. washthe solid precipitate is washed with ether and benzene
  5. customThe solid is collected
  6. extractionThe mixture is extracted with ether
  7. extractionthe ether extract
  8. washis washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationAfter filtration
  11. customthe ether is removed
  12. customto give a crystalline residue which
  13. customis recrystallized from methanol

Sources & evidence

ORD record
ord-d5d36e5f5746468588a98ff9adac1be1
Source dataset
uspto-grants-1977_08
Patent number
US04044143

Reaction notes

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