Sodium Hydroxide → HCID 14879930, compound

HRID 1709651Notes

Reaction equation

HRID 1709651 reaction equation
[C:1]1([C:7]2[CH:17]=[CH:16][C:10]([CH2:11][C:12](=[CH2:15])[CH2:13]Cl)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][CH:19]1[CH2:24][CH:23]([CH3:25])[CH2:22][NH:21][CH2:20]1.[OH-].[Na+]>>[C:1]1([C:7]2[CH:17]=[CH:16][C:10]([CH2:11][C:12](=[CH2:15])[CH2:13][N:21]3[CH2:22][CH:23]([CH3:25])[CH2:24][CH:19]([CH3:18])[CH2:20]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 1182593,5-DimethylpiperidineHCID 54122074HCID 54122074, compound

Product 1

HCID 14879930HCID 14879930, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 2-[(4-phenyl)benzyl]-2-propenyl chloride (4 g.), synthesized by method utilized in Example 1, and 3,5-dimethylpiperidine (3.7 g.) was heated at 120° C. for five hours. The mixture was cooled to room temperature and neutralized with 25% aqueous sodium hydroxide (15 ml.). The mixture was extracted with toluene, dried over sodium sulfate and evaporated to give an oil which partially solidified on standing. The product was triturated with petroleum ether, having a boiling point range of 30° C. to 60° C., and the insoluble material was removed by filtration. The filtrate was evaporated under reduced pressure to yield 1-[2-[(4-phenyl)benzyl]-2-propenyl]-3,5-dimethylpiperidine in a yield of 4.9 grams.

Workup

  1. customsynthesized by method
  2. extractionThe mixture was extracted with toluene
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customto give an oil which
  6. customThe product was triturated with petroleum ether
  7. customa boiling point range of 30° C. to 60° C.
  8. customthe insoluble material was removed by filtration
  9. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-51c67ceaf98946bc8f2302cc219df357
Source dataset
uspto-grants-1990_08
Patent number
US04950671

Reaction notes

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