Pyrrolidine → 5-Benzyloxy-2-[2-(1-pyrrolidinyl)ethyl]4-pyridone

HRID 1734252

Reaction equation

HRID 1734252 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH2:11][C:12]([CH:15]=[CH2:16])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCCC1.C(OC(C)C)(C)C>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH2:11][C:12]([CH2:15][CH2:16][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 677480895-Benzyloxy-2-vinyl-4-pyridone

Product 1

HCID 677480915-Benzyloxy-2-[2-(1-pyrrolidinyl)ethyl]4-pyridone

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-benzyloxy-2-vinyl-4-pyridone (2.90 g) and pyrrolidine (5.33 ml) was heated and refluxed for an hour. The mixture was cooled and diluted with tetrahydrofuran (20 ml) and diisopropyl ether (80 ml). After being stirred for an hour at ambient temperature, the resulting precipitate was collected by filtration, washed with diisopropyl ether and air-dried at ambient temperature to give 5-benzyloxy-2-[2-(1-pyrrolidinyl)ethyl]-4-pyridone (3.79 g).

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for an hour
  3. temperatureThe mixture was cooled
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with diisopropyl ether
  6. customair-dried at ambient temperature

Sources & evidence

ORD record
ord-7dd94348d6ef4806be9e10a7289f9faa
Source dataset
uspto-grants-1996_07
Patent number
US05532354

Linked notes

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