Sodium Hydroxide → 4-Methyl-1-(2-nitrophenyl)piperazine-2-carboxylic acid

HRID 1390364Notes

Reaction equation

HRID 1390364 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH:8]1[CH2:13][N:12]([CH3:14])[CH2:11][CH2:10][NH:9]1)=[O:7])C.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1F)([O-:17])=[O:16]>O.C(O)C>[CH3:14][N:12]1[CH2:11][CH2:10][N:9]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N+:15]([O-:17])=[O:16])[CH:8]([C:6]([OH:5])=[O:7])[CH2:13]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 738951-Fluoro-2-nitrobenzeneHCID 12558522Ethyl 4-methylpiperazine-2-carboxylate

Product 1

HCID 203786594-Methyl-1-(2-nitrophenyl)piperazine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 6.6 g. (0.164 mole) of sodium hydroxide, 28.2 g. (0.165 mole) of ethyl-4-methylpiperazine-2-carboxylate, 20 ml. of water and 200 ml. of ethanol is refluxed for 3 hours. This solution is then added under nitrogen to a hot stirred solution of o-nitrofluorobenzene in 300 ml. of ethanol and 30 ml. of water. The resultant solution is refluxed for 48 hours, cooled and filtered to give 12.8 g. of yellow product, m.p. 222°-225°. Concentration of the mother liquors to ~100 ml. and adjusting the pH to 6 yields an additional 6.6 g. of product. Further concentration of mother liquors gives yet another 3 g. of product. Total yield is 22.4 g., 51.5%. The analytical sample had m.p. 234° dec.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customto give 12.8 g
  4. customyields an additional 6.6 g
  5. concentrationFurther concentration of mother liquors
  6. customgives yet another 3 g

Sources & evidence

ORD record
ord-d1c1b8e73acb44bebe04ad71ae279013
Source dataset
uspto-grants-1979_02
Patent number
US04138567

Reaction notes

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