2-(Phenylmethyl)pyridine → HCID 22220846, compound

HRID 1836740Notes

Reaction equation

HRID 1836740 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:14][CH2:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17]>C(#N)C.CO>[Br-:14].[N:18]1([C:16](=[O:17])[CH2:15][N+:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 75812-(Phenylmethyl)pyridineHCID 111061881-(Bromoacetyl)pyrrolidine

Product 1

HCID 22220846HCID 22220846, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Conditions

Temperature
98 °C

Procedure

2-Benzylpyridine (1.0 g, 5.9 mmole) and 1-(bromoacetyl)pyrrolidine (1.134 g, 5.9 mmole) were heated with stirring in an oil bath at 98° C. for 2 hr. The viscous mixture was dissolved in 10 mL 4:1 acetonitrile-methanol and stored at 4° C. for 2 days. The crystals which separated were filtered out to give 1.96 g of crude product which was recrystalized from methanol-acetonitrile to give 1.45 g of the title compound, mp 224-226° C.

Workup

  1. waitstored at 4° C. for 2 days
  2. customThe crystals which separated
  3. filtrationwere filtered out
  4. customto give 1.96 g of crude product which
  5. customwas recrystalized from methanol-acetonitrile

Sources & evidence

ORD record
ord-54216ed7dd8f4da090d6b76842bee611
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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