Allyl bromide → 1-(4-Allyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanol

HRID 370664Notes

Reaction equation

HRID 370664 reaction equation
[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[OH:16])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:30](Br)[CH:31]=[CH2:32].[OH-].[K+]>C(O)C>[CH2:32]([O:23][C:20]1[CH:19]=[CH:18][C:17]([CH:15]([OH:16])[CH2:14][N:11]2[CH2:10][CH2:9][N:8]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:13][CH2:12]2)=[CH:22][CH:21]=1)[CH:31]=[CH2:30]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 30711602-(4-Diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanol

Product 1

HCID 103203901-(4-Allyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanolYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 1.2 liters of ethanol were dissolved 120 g (0.31 mol) of 2-(4-diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)-ethanol, 74.8 g (0.62 mol) of allyl bromide and 41 g of potassium hydroxide. The resultant solution was heated with refluxing for one hour. After cooling the solution and then removing the solvent, the residue was added with 1.0 liter of ethyl acetate. The resultant mixture was washed successively with an aqueous 1N solution of sodium hydroxide, water and saturated saline, followed by drying over anhydrous sodium sulfate. The solvent was removed, and the residue was crystallized from a mixed solvent of ethanol and n-hexane to give 84.6 g of 1-(4-allyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanol (yield: 64%).

Workup

  1. temperaturewith refluxing for one hour
  2. temperatureAfter cooling the solution
  3. customremoving the solvent
  4. additionthe residue was added with 1.0 liter of ethyl acetate
  5. washThe resultant mixture was washed successively with an aqueous 1N solution of sodium hydroxide, water and saturated saline
  6. dry with materialby drying over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. customthe residue was crystallized from a mixed solvent of ethanol and n-hexane

Sources & evidence

ORD record
ord-0aac2fb3855742bda7200f6e4e9e1e46
Source dataset
uspto-grants-1985_07
Patent number
US04528194

Reaction notes

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