Pyridine → 1-BENZYL-1,2,3,6-TETRAHYDROPYRIDINE

HRID 1505647Notes

Reaction equation

HRID 1505647 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[BH4-].[Na+]>C(#N)C>[CH2:1]([N:9]1[CH2:10][CH:11]=[CH:12][CH2:13][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7498Benzyl BromideHCID 4311764Sodium borohydride

Product 1

HCID 64215731-BENZYL-1,2,3,6-TETRAHYDROPYRIDINE

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
71 °C

Procedure

2.4 mL of benzyl bromide (20 mmol) was added dropwise over an hour to a solution of 1.6 mL of pyridine in 5 mL of acetonitrile. Then reaction mixture was heated at 70 to 72° C. for 3 hours. Solvent was removed under reduced pressure and the residue was dissolved in 16 mL of ethanol. 1.1 g of sodium borohydride (30 mmol) was added in small portions over 30 minutes. After stirring for 24 hs reaction mixture was carefully quenched with 50 mL of water and solvents were removed in vacuo. The residue was portioned between ethyl acetate and 2M NaOH solution. Organic extracts were washed with brine, dried over MgSO4 and evaporated to afford crude 3.36 g of crude 1-benzyl-1,2,3,6-tetrahydropyridine which was used in the next step without purification.

Workup

  1. customThen reaction mixture
  2. customSolvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in 16 mL of ethanol
  4. customwas carefully quenched with 50 mL of water and solvents
  5. customwere removed in vacuo
  6. washOrganic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-541a61fa2f884180bc138b5687b9eb3f
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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