Hydrochloric Acid → HCID 12368887, compound

HRID 1283320Notes

Reaction equation

HRID 1283320 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

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-006f46e2159647bcb3b59066976f649c
Source dataset
uspto-grants-1976_08
Patent number
US03974285

Reaction notes

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