HCID 19595241, compound → HCID 19595168, compound

HRID 612480Notes

Reaction equation

HRID 612480 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]([NH:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[N:23]1[CH:24]=[CH:25][C:20]([NH:19][N:15]2[CH2:14][CH2:13][C:12]3[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=3)[CH2:16]2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 19595241HCID 19595241, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19595168HCID 19595168, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-benzyloxy-2-(4-pyridinylamino)-1,2,3,4-tetrahydroisoquinoline (5.68 g) and 5% palladium-on-carbon (1.1 g) in methanol (85 mL) was shaken on a parr hydrogenation apparatus at ambient temperature, starting at an initial pressure of 55 psi. After 2 hrs an additional 1.1 g of catalyst was added, the pressure was increased to 55 psi, and the mixture was shaken for an additional 5 hrs. An additional 0.75 g of catalyst was added, the pressure was increased to 55 psi, and the mixture was shaken until hydrogen uptake ceased. The reaction mixture was filtered through a pad of Celite, and the pad was washed with methanol. Concentration of the filtrate gave 3.4 g (82%) of product. Recrystallization from ethanol gave the analytical sample, mp 236-239° C. (dec).

Workup

  1. temperaturethe pressure was increased to 55 psi
  2. stirringthe mixture was shaken for an additional 5 hrs
  3. temperaturethe pressure was increased to 55 psi
  4. filtrationThe reaction mixture was filtered through a pad of Celite
  5. washthe pad was washed with methanol

Sources & evidence

ORD record
ord-1e419e1df7bc41b3b17c0c91c1950d2b
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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