Hydrochloric Acid → HCID 10180924, compound

HRID 1359073Notes

Reaction equation

HRID 1359073 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[O:16][CH2:15][C@H:14]([CH2:17][N:18]4[CH2:23][CH:22]=[C:21]([C:24]5[C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[NH:26][CH:25]=5)[CH2:20][CH2:19]4)[O:13][C:9]3=2)[N:4]=1)[CH3:2].Cl.[H][H]>[Pd].CO>[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[O:16][CH2:15][CH:14]([CH2:17][N:18]4[CH2:19][CH2:20][CH:21]([C:24]5[C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[NH:26][CH:25]=5)[CH2:22][CH2:23]4)[O:13][C:9]3=2)[N:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12042432HCID 12042432, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10180924HCID 10180924, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 0.25 g (0.59 mmole) of (2S)-8-ethyl-2-[(4-(1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl)methyl]-2,3-dihydro[1,4]dioxino[2,3-f]quinoline and 0.2 g of 10% palladium on carbon in 100 mL of methanol was added 0.2 mL of concentrated HCl. The mixture was treated with 60 psi of hydrogen in a Parr apparatus for 15 hours. It was then filtered through celite and concentrated to an oil in vacuum. Ethyl acetate (300 mL) was added and the mixture was washed with 300 mL portions of saturated aqueous sodium bicarbonate and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. Column chromatography on silica gel with 0-2% methanol/chloroform as eluant gave 0.19 g of the title compound as the free base. Recrystallization from ethanol with the addition of 0.052 g of fumaric acid gave 0.15 g of the (S)-enantiomer of the title compound as an off-white fumarate (m.p. 169-172° C.).

Workup

  1. filtrationIt was then filtered through celite
  2. concentrationconcentrated to an oil in vacuum
  3. additionEthyl acetate (300 mL) was added
  4. washthe mixture was washed with 300 mL portions of saturated aqueous sodium bicarbonate and saturated brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-149cf727a5b24ba884f199dd138ff631
Source dataset
uspto-grants-2003_07
Patent number
US06599915B2

Reaction notes

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