Hydrochloric Acid → HCID 68827479, compound

HRID 1987229Notes

Reaction equation

HRID 1987229 reaction equation
Cl.C([N:9]1[CH2:17][C@H:16]2[C@H:11]([CH2:12][C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[CH2:15]2)[CH2:10]1)C1C=CC=CC=1.Cl.O1CCOCC1.[H][H]>C(O)C.[OH-].[Pd+2].[OH-]>[CH2:10]1[C@H:11]2[C@H:16]([CH2:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[CH2:12]2)[CH2:17][NH:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid3×HCID 312751,4-DioxaneHCID 68827224HCID 68827224, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 68827479HCID 68827479, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst3×HCID 702EthanolSolvent

Procedure

To a solution of cis-2-benzyl-2,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole hydrochloride (210 mg, 0.80 mmol) in 10 mL of ethanol was added palladium hydroxide (210 mg, 20 wt % on carbon) and 4 N hydrochloric acid solution in dioxane (1 mL, 4 mmol). The mixture was placed on a Parr apparatus, the vessel was pressurized to 50 psi with hydrogen, and the mixture was shaken for 2 days. TLC of the mixture showed very little reaction, so the same amounts of palladium hydroxide and hydrochloric acid were added again. The vessel was pressurized to 50 psi with hydrogen, and the mixture was shaken for an additional 3 days. TLC of the mixture showed that the reaction was still incomplete, and so the same amounts of palladium hydroxide and hydrochloric acid were added, the vessel was pressurized to 50 psi with hydrogen, and the mixture was shaken for an additional 6 days. The mixture was filtered through celite, and the cake was rinsed with methanol. The filtrate was stripped, the residue was taken up in 20 mL of 1 N sodium hydroxide, and the aqueous was extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and stripped to yield 90 mg of an amber oil, which was purified by flash chromatography, eluting with ethyl acetate followed by 20% methanol/chloroform. Obtained 35 mg of a colorless oil. Yield=25%. NMR (300 MHz, CDCl3) δ 7.17-7.09 (m, 4H), 3.17-3.16 (m, 2H), 2.79 (bd, 2H, J=9 Hz), 2.58-2.43 (m, 6H), 2.36 (s, 1H).

Workup

  1. customreaction
  2. stirringthe mixture was shaken for an additional 3 days
  3. stirringthe mixture was shaken for an additional 6 days
  4. filtrationThe mixture was filtered through celite
  5. washthe cake was rinsed with methanol
  6. extractionthe aqueous was extracted with ethyl acetate
  7. dry with materialThe combined extracts were dried over sodium sulfate

Sources & evidence

ORD record
ord-f286dadb401b40bc90ab87279f21d4e5
Source dataset
uspto-grants-2009_06
Patent number
US07550500B2

Reaction notes

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