HCID 53882425, compound → HCID 19595122, compound

HRID 612464Notes

Reaction equation

HRID 612464 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([N:19]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[CH3:20])[CH2:13][CH2:12]2)C1C=CC=CC=1>CO.[Pd]>[CH3:20][N:19]([C:21]1[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=1)[N:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=2)[CH2:15]1

Participants

4

Reactant 1

HCID 53882425HCID 53882425, compound

Product 1

HCID 19595122HCID 19595122, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-benzyloxy-3,4-dihydro-1H-isoquinoline-2-yl-N-methyl-4-pyridinylamine (5.1 g) and 5% palladium-on-carbon (1.0 g) in methanol (75 ml) was shaken on a Parr hydrogenation apparatus at ambient temperature and an initial pressure of 55 psi for 2 hrs. An additional 1 g of catalyst was added, and the mixture was shaken for an additional 4 hrs at an initial pressure of 55 psi. The reaction mixture was filtered through a pad of celite, the pad was washed with methanol, and the filtrate was concentrated to give 3.45 g (92%) of product. Recrystallization from methanol provided the analytical sample, mp 263-266° C.

Workup

  1. stirringthe mixture was shaken for an additional 4 hrs at an initial pressure of 55 psi
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washthe pad was washed with methanol
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-975e530580a84d548428a74a5aca0081
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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