HCID 20391675, compound → HCID 13308996, compound

HRID 1863483Notes

Reaction equation

HRID 1863483 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH:14]=[C:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH:19]=[CH:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:9]1)C1C=CC=CC=1>C(O)(=O)C.[Pd].Cl>[NH:8]1[CH2:13][CH2:12][O:11][CH:10]([CH:14]=[C:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:9]1

Participants

5

Reactant 1

HCID 20391675HCID 20391675, compound

Product 1

HCID 13308996HCID 13308996, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 5-(4-benzylmorpholin-2-yl)methylidene-5H-dibenzo[a,d]cycloheptene (0.32 g) in acetic acid was added to 10% palladium on charcoal (90 mg) pretreated under hydrogen in hydrochloric acid, and the resulting mixture was stirred under hydrogen at room temperature for 8 hours. After elimination of the catalyst by filtration, the filtrate was evaporated. The residue was neutralized with 10% aqueous sodium hydroxide solution and extracted with chloroform. The chloroform extract was washed with water, dried and evaporated to afford 5-(morpholin-2-yl)methylidene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as oily material. M.P., 221°-224° (oxalate).

Workup

  1. filtrationAfter elimination of the catalyst by filtration
  2. customthe filtrate was evaporated
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. washwas washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-7ea6300fc5384c1d809df4db30dacec3
Source dataset
uspto-grants-1979_09
Patent number
US04169146

Reaction notes

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