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

HRID 1065219Notes

Reaction equation

HRID 1065219 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-e09731b1aa25460a92e933850841e5c1
Source dataset
uspto-grants-1982_05
Patent number
US04329289

Reaction notes

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