1,2,3,6-Tetrahydropyridine → naphthalen-2-ylmethyl 5,6-dihydropyridine-1(2H)-carboxylate

HRID 1095712Notes

Reaction equation

HRID 1095712 reaction equation
[C:1](Cl)(=[O:14])[O:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.[NH:16]1[CH2:21][CH:20]=[CH:19][CH2:18][CH2:17]1.C([O-])(O)=O.[Na+]>C1COCC1.O>[N:16]1([C:1]([O:2][CH2:3][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=2)=[O:14])[CH2:21][CH2:20][CH:19]=[CH:18][CH2:17]1

Participants

6

Reactant 3

HCID 127501,2,3,6-TetrahydropyridineHCID 516892Sodium BicarbonateHCID 15764399(Naphthalen-2-yl)methyl carbonochloridate

Product 1

HCID 66781418naphthalen-2-ylmethyl 5,6-dihydropyridine-1(2H)-carboxylateYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Naphthalen-2-ylmethyl carbonochloridate (11.00 g, 49.85 mmol) was dissolved in THF (25 mL) and this was added dropwise to a cooled (0° C.) solution of 1,2,3,6-tetrahydropyridine (3.79 ml, 41.5 mmol) and NaHCO3 (4.18 g, 49.8 mmol) in water (88 mL). A precipitate formed in the reaction immediately, therefore after the addition, additional THF (63 mL) was added to solubilize the reaction mixture. The solution was removed from the bath and warmed to ambient temperature for 16 hours. The reaction was concentrated in vacuo then methylene chloride was added. The mixture was separated, the aqueous layer was washed with methylene chloride, and the combined organics were dried over Na2SO4 and concentrated in vacuo to provide the desired product as an oil (11 g).

Workup

  1. additionthis was added dropwise to
  2. customA precipitate formed in the reaction immediately
  3. additionwas added
  4. customThe solution was removed from the bath
  5. concentrationThe reaction was concentrated in vacuo
  6. additionmethylene chloride was added
  7. customThe mixture was separated
  8. washthe aqueous layer was washed with methylene chloride
  9. dry with materialthe combined organics were dried over Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83b1276f69e045f39557c036f0f36b0a
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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