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

HRID 1609649

Reaction equation

HRID 1609649 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-10f54cffd5024a99aff0992064e5c140
Source dataset
uspto-grants-1995_03
Patent number
US05401734

Linked notes

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