4-Nitrophenethyl bromide → HCID 21278908, compound

HRID 2291554Notes

Reaction equation

HRID 2291554 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([CH2:23][CH2:24]Br)=[CH:21][CH:20]=1)([O-:18])=[O:17].C(=O)(O)[O-].[Na+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:24][CH2:23][C:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:27][CH:26]=3)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 792664-Nitrophenethyl bromideHCID 804471-(4-Nitrophenyl)piperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 21278908HCID 21278908, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Nitrophenyl)piperazine (4.14 g), 4-nitrophenethyl bromide (4.6 g) and sodium bicarbonate (3.4 g) in acetonitrile (75 ml) were stirred under reflux for 1 day, and then evaporated to dryness. The residue was then triturated with water (300 ml), filtered, washed with water (300 ml), and the resulting solid was crystallized from ethyl acetate, yielding the title compound, (3.62 g), m.p. 143°-5°.

Workup

  1. temperatureunder reflux for 1 day
  2. customevaporated to dryness
  3. customThe residue was then triturated with water (300 ml)
  4. filtrationfiltered
  5. washwashed with water (300 ml)
  6. customthe resulting solid was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e63737c15b52421c9b44c8bdf286a04f
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

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