6-Benzyl-5-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-[1,6]naphthyridine → 5-[2-(4-Methoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-[1,6]naphthyridine

HRID 563927Notes

Reaction equation

HRID 563927 reaction equation
C([N:8]1[CH:17]=[CH:16][C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:9]1[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)C1C=CC=CC=1>CO.C(O)(=O)C.[Pd]>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][CH:9]2[NH:8][CH2:17][CH2:16][C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]2=3)=[CH:21][CH:22]=1

Participants

5

Reactant 1

HCID 598200166-Benzyl-5-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-[1,6]naphthyridine

Product 1

HCID 598199895-[2-(4-Methoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-[1,6]naphthyridineYield 93.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 2.1 g (5.85 mmol) 6-benzyl-5-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-[1,6]naphthyridine in 70 mL methanol and 7 mL acetic acid was added 210 mg Pd/C 10% and hydrogenated at atmospheric pressure for 4 h at 55° C. The apparatus was purged with argon, the catalyst was filtered and the filtrate was concentrated in vacuo. The oil was dissolved in ethyl acetate and the solution was washed once with a sat. NaHCO3 solution. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to yield 1.47 g (93%) of the title compound was yielded as yellow oil.

Workup

  1. customThe apparatus was purged with argon
  2. filtrationthe catalyst was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe oil was dissolved in ethyl acetate
  5. washthe solution was washed once with a sat. NaHCO3 solution
  6. extractionThe aqueous layer was extracted twice with ethyl acetate
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-092e02344dc2446b882ae54982218f08
Source dataset
uspto-grants-2011_11
Patent number
US08067598B2

Reaction notes

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