HCID 10405241, compound → HCID 18409110, compound

HRID 1033512Notes

Reaction equation

HRID 1033512 reaction equation
[C:1]1([CH2:7][C:8]2([NH2:26])[CH2:17][CH2:16][CH2:15][C:14]3[N:13]=[C:12]([O:18]CC4C=CC=CC=4)[CH:11]=[CH:10][C:9]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(O)C.[ClH:31].[H][H]>C(O)C.[Pd]>[ClH:31].[NH2:26][C:8]1([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:17][CH2:16][CH2:15][C:14]2[NH:13][C:12](=[O:18])[CH:11]=[CH:10][C:9]1=2

Participants

6

Reactant 3

HCID 10405241HCID 10405241, compoundHCID 21912024Isopropanol hydrochlorideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 18409110HCID 18409110, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5,6,7,8-tetrahydro-5-(phenylmethyl)-2-(phenylmethoxy)-5-quinolinamine (19.1 g) and 10% palladium-on-carbon (1.5 g) in ethanol (1 l) was acidified to about pH 2-3 with 2-propanol/hydrochloric acid solution. The mixture was shaken on Parr hydrogenation apparatus, starting at 55 psi of hydrogen, until hydrogen uptake ceased. The catalyst was removed by filtration, the filtrate was neutralized with 4-polyvinylpyridine and concentrated. The residue was triturated with a mixture of methanol and ethyl acetate. The precipitate was collected and recrystallized form water/methanol/ethyl acetate to afford 4.6 g (28%) of product, mp 235°-238° C. (dec), in two crops.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationconcentrated
  3. customThe residue was triturated with a mixture of methanol and ethyl acetate
  4. customThe precipitate was collected
  5. customrecrystallized
  6. customform water/methanol/ethyl acetate

Sources & evidence

ORD record
ord-bc503ac168254ddc80c16b820561ff23
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

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