Sodium Hydroxide → HCID 14879929, compound

HRID 1709650Notes

Reaction equation

HRID 1709650 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][CH2:23][NH:22][CH2:21][CH2:20]1.[OH-].[Na+]>CC1C=CC(C)=CC=1>[C:1]1([C:7]2[CH:17]=[CH:16][C:10]([CH2:11][C:12](=[CH2:15])[CH2:13][N:22]3[CH2:23][CH2:24][CH:19]([CH3:18])[CH2:20][CH2:21]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 693814-MethylpiperidineHCID 54122074HCID 54122074, compound

Product 1

HCID 14879929HCID 14879929, compound

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A mixture of 2-[(4-phenyl)benzyl]-2-propenyl chloride (4 g.), formed in a manner analogous to that used in Example 1, and 4-methylpiperidine (3.3 g.) in p-xylene (15 ml.) was refluxed for five hours, cooled and neutralized with 25% aqueous sodium hydroxide (15 ml.). The mixture was extracted with toluene, dried over sodium sulfate and evaporated under reduced pressure to give an oil. The oil was distilled under vacuum and the fraction boiling at 195° C. to 200° C. at a pressure of 0.7 mm Hg. was collected and identified as 1-[2-[(4-phenyl)benzyl]-2-propenyl]-4-methylpiperidine. The compound, obtained in a yield of 3.5 g., solidified after being left at room temperature for a few hours. The solid was characterized by a melting point of 53° C.

Workup

  1. customformed in a manner analogous to
  2. temperaturewas refluxed for five hours
  3. temperaturecooled
  4. extractionThe mixture was extracted with toluene
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. distillationThe oil was distilled under vacuum
  9. customwas collected
  10. customThe compound, obtained in a yield of 3.5 g
  11. waitafter being left at room temperature for a few hours

Sources & evidence

ORD record
ord-2308a9aacc254fe18f7e0e390450661f
Source dataset
uspto-grants-1990_08
Patent number
US04950671

Reaction notes

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