Hydrochloric Acid → Hydrochloric Acid

HRID 442522Notes

Reaction equation

HRID 442522 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][C:15]23[CH2:30][CH2:29][CH:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=42)[C:21]2[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:9]1)C1C=CC=CC=1.[ClH:31]>C(O)(=O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][C:15]23[CH2:30][CH2:29][CH:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=42)[C:21]2[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:9]1.[ClH:31]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21415009HCID 21415009, compound

Product 2

HCID 313Hydrochloric AcidHCID 21415024HCID 21415024, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 9-(4-benzyl-2-morpholinylmethyl)-9,10-dihydro-9,10-ethanoanthracene (150 mg) in acetic acid was added to 10% palladium on charcoal (60 mg) pretreated under hydrogen in hydrochloric acid, and the resulting mixture was stirred under hydrogen at room temperature for 14 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 over anhydrous sodium sulfate and evaporated to dryness. The residue was purified over silica gel chromatography to give 9-(2-morpholinylmethyl)-9,10-dihydro-9,10-ethanoanthracene, M.P. 242° - 244° C. (hydrochloride).

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. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified over silica gel chromatography

Sources & evidence

ORD record
ord-537313cc5d984ecf969228fbc7b2eaec
Source dataset
uspto-grants-1977_08
Patent number
US04045560

Reaction notes

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