Triethylamine → 7-Benzyl-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile

HRID 1052078Notes

Reaction equation

HRID 1052078 reaction equation
[CH2:1]([N:8]1[CH2:17][C:16]2[C:15](Cl)=[N:14][C:13](Cl)=[C:12]([C:20]#[N:21])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CO.ClCCl.[Pd]>[CH2:1]([N:8]1[CH2:17][C:16]2[CH:15]=[N:14][CH:13]=[C:12]([C:20]#[N:21])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 5619007-Benzyl-1,3-dichloro-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile

Product 1

HCID 847069997-Benzyl-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrileYield 88.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-benzyl-1,3-dichloro-5,6,7,8-tetrahydro-[2,7]-naphthyridine-4-carbonitrile (70 g, 0.22 mol) and triethylamine (70 mL) in methanol (1 L) was placed in a 2.5 L hydrogenation bottle and hydrogenated over 10% Pd/C (15 g) for 3 hr. The reaction mixture was filtered to remove catalyst. The catalyst on filter paper was washed with methanol (100 mL). The filtrate was concentrated under reduced pressure to give an oil. The oil was dissolved in dichloromethane (500 mL), washed with water (2×200 mL), brine (200 mL), dried over anhydrous magnesium sulfate (10 g), filtered and concentrated under reduced pressure to give an oil. The oil was placed under high vacuum line overnight to give the title compound (48.5 g, 88%). 1H NMR 60 MHz, (CDCl3), δ 8.5 (s, 1H), 8.3 (s, 1H), 7.3 (s, 5H), 3.7 (s, 2H), 3.6 (s, 2H), 2.8 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove catalyst
  3. filtrationThe catalyst on filter paper
  4. washwas washed with methanol (100 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give an oil
  7. washwashed with water (2×200 mL), brine (200 mL)
  8. dry with materialdried over anhydrous magnesium sulfate (10 g)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto give an oil
  12. customwas placed under high vacuum line overnight

Sources & evidence

ORD record
ord-c19b400a209840ea9282dbcc8baf1cdd
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

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