Ethylene Glycol → HCID 751653, compound

HRID 1390974Notes

Reaction equation

HRID 1390974 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.Cl.CO[N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.C(N(CC)CC)C.C(O)[CH2:36][OH:37]>>[CH3:36][O:37][C:25]1[CH:24]=[CH:23][C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH2:8][C:7]3[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:21][CH2:20]2)=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 74824-Nitrobenzyl chlorideHCID 8471TriethylamineHCID 70608515HCID 70608515, compound

Product 1

HCID 751653HCID 751653, compoundYield 81%

Conditions

Temperature
80 °C

Procedure

A suspension of p-nitrobenzyl chloride (2.58 g, 15 mM), p-methoxyphenylpiperazine dihydrochloride (3.97 g, 15 mM) and triethylamine (4.55 g, 30 mM) in 25 ml of ethylene glycol is heated at 80° C. for 1 hour under nitrogen. The resulting mixture is quenched with cold water, neutralized with 10% aqueous sodium bicarbonate solution and extracted with methylene chloride. The methylene chloride solution is washed with water, saturated sodium chloride solution, dried over sodium sulfate and concentrated to a yellow solid. This, after recrystallization from ethyl acetate, gives 4 g (81%) of 1-(4-methoxyphenyl)-4-[ (4-nitrophenyl)-methyl ]piperazine of melting point 130° -132° C.

Workup

  1. customThe resulting mixture is quenched with cold water
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride solution is washed with water, saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a yellow solid
  6. customThis, after recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d1eae5e2dc644dddb4303ff470cfaa80
Source dataset
uspto-grants-1979_02
Patent number
US04140775

Reaction notes

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