Sodium hydride → HCID 13672472, compound

HRID 1165756Notes

Reaction equation

HRID 1165756 reaction equation
[H-].[Na+].[NH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][OH:8].Br[C:10]1[CH:15]=[C:14]([CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:13]=[CH:12][N:11]=1>O1CCCC1>[CH2:20]1[CH2:21][CH2:22][N:17]([CH2:16][C:14]2[CH:13]=[CH:12][N:11]=[C:10]([O:8][CH2:7]/[CH:6]=[CH:5]/[CH2:4][NH2:3])[CH:15]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10153997HCID 10153997, compoundHCID 136724712-Bromo-4-[(piperidin-1-yl)methyl]pyridine

Product 1

HCID 13672472HCID 13672472, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.78 g of 60% sodium hydride was suspended in 20 ml of anhydrous tetrahydrofuran, and 1.54 g (17.7 mM) of 4-amino-cis-2-buten-1-ol was slowly added. The mixture was refluxed with stirring for 20 minutes. Then, under ice cooling, a solution of 3.00 g (11.8 mM) of 2-bromo-4-(piperidinomethyl)pyridine in 10 ml of tetrahydrofuran was added slowly to the mixture, and the entire mixture was then refluxed for 48 hours with stirring. After the reaction, the insoluble matter was removed by filtration, and the solvent was evaporated from the filtrate. The residue was extracted with 100 ml of dichloromethane three times. The extracts were dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography using a 1:3 mixture of methanol and ethyl acetate as an eluent to give 1.49 g (yield 48%) of the compound as a pale brown oil.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturethe entire mixture was then refluxed for 48 hours
  3. stirringwith stirring
  4. customAfter the reaction
  5. customthe insoluble matter was removed by filtration
  6. customthe solvent was evaporated from the filtrate
  7. extractionThe residue was extracted with 100 ml of dichloromethane three times
  8. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography
  11. additiona 1:3 mixture of methanol and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-5391e1a1159e46f6a0f3be7c81dc5d9c
Source dataset
uspto-grants-1990_03
Patent number
US04912101

Reaction notes

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