Monobenzone → 1-[2-(4-Benzyloxyphenoxy)ethyl]-4-phenylpiperazine

HRID 1659461Notes

Reaction equation

HRID 1659461 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1>CS(C)=O.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7638MonobenzoneHCID 47418781-(2-Chloroethyl)-4-phenylpiperazine

Product 1

HCID 129411031-[2-(4-Benzyloxyphenoxy)ethyl]-4-phenylpiperazine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

26.25 ml 4 N NaOH (0.105 mol) was added to a stirred mixture of 21.0 g (0.105 mol) 4-benzyloxyphenol and 22.5 g (0.1 mol) of 1-(2-chloroethyl)-4-phenylpiperazine in 250 ml DMSO and the reaction was heated at 60° for 60 min. After cooling, the stirred mixture was diluted with 50 ml 1 N NaOH solution and the resulting crystalline precipitate was collected by filtration and washed with water to give, after drying in vacuo, essentially pure end product, mp 116°-119°.

Workup

  1. temperaturethe reaction was heated at 60° for 60 min
  2. temperatureAfter cooling
  3. filtrationthe resulting crystalline precipitate was collected by filtration
  4. washwashed with water
  5. customto give
  6. customafter drying in vacuo, essentially pure end product, mp 116°-119°

Sources & evidence

ORD record
ord-bcb77744ff2b4b61aba59e882c6a6e4b
Source dataset
uspto-grants-1981_12
Patent number
US04304721

Reaction notes

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