3-Chloro-4-methylaniline → 1-(3-chloro-4-methylphenyl)piperazine

HRID 1727202Notes

Reaction equation

HRID 1727202 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[NH:10]([CH2:14][CH2:15]O)[CH2:11][CH2:12]O>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:15][CH2:14][NH:10][CH2:11][CH2:12]2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 72553-Chloro-4-methylanilineHCID 8113Diethanolamine

Product 1

HCID 4130921-(3-chloro-4-methylphenyl)piperazineYield 68.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
240 °C

Procedure

To a mixture of 3-chloro-4-methylaniline (105.5 g, 0.745 mol) and diethanolamine (78.1 g, 0.745 mol) was added slowly with stirring and cooling, concentrated hydrochloric acid (c.a. 100 ml) to adjust the reaction mixture to pH 7. The reaction mixture was heated to remove water (66 ml), after standing for 18 h the mixture was heated to 240° C. for 6 h. Sodium hydroxide (5N, solution, 236 ml) was added and the product was extracted with chloroform (4×100 ml). The combined organic extracts were concentrated to give a red oil which was purified by distillation to give the title compound (107.0 g, 68%)

Workup

  1. additionwas added slowly
  2. temperaturecooling
  3. temperatureThe reaction mixture was heated
  4. customto remove water (66 ml)
  5. additionSodium hydroxide (5N, solution, 236 ml) was added
  6. extractionthe product was extracted with chloroform (4×100 ml)
  7. concentrationThe combined organic extracts were concentrated
  8. customto give a red oil which
  9. distillationwas purified by distillation

Sources & evidence

ORD record
ord-2ba46ce803e6405abc014fd768e1be3c
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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