HCID 14476572, compound → HCID 14476574, compound

HRID 654137Notes

Reaction equation

HRID 654137 reaction equation
[CH3:1][N:2](CC1C=CC=CC=1)[C@@H:3]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C@H:4]1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CO.[Pd]>[CH3:1][NH:2][C@@H:3]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C@H:4]1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 14476572HCID 14476572, compound

Product 1

HCID 14476574HCID 14476574, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2 g of the product of Step B in 40 ml of methanol and 2.6 ml of 22 Be hydrochloride acid was hydrogenated with 1.25 g of palladium under 1800 mmbars for 45 minutes. The mixture was filtered, rinsed with methanol and concentrated under reduced pressure at 50° C. The residue was dissolved in 10 ml of water which was alkalized with 2.6 ml of sodium hydroxide solution, and extracted with methylene chloride. The extracts were washed with water, dried, filtered and concentrated under reduced pressure to obtain 1.45 g of yellow oil which was dissolved in isopropyl ether. The insoluble substance was filtered and the residue was treated with active charcoal, filtered and concentrated to dryness under reduced pressure at 50° C. to obtain 1.24 g of the expected product.

Workup

  1. filtrationThe mixture was filtered
  2. washrinsed with methanol
  3. concentrationconcentrated under reduced pressure at 50° C
  4. dissolutionThe residue was dissolved in 10 ml of water which
  5. extractionextracted with methylene chloride
  6. washThe extracts were washed with water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b80f5f33bbb342629f62b195fcc82efa
Source dataset
uspto-grants-1992_07
Patent number
US05130329

Reaction notes

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