Hydrazine hydrate (1:1) → 4-[4-(Trifluoromethyl)phenyl]-1-piperazineethanamine

HRID 856080Notes

Reaction equation

HRID 856080 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]3C(=O)C4=CC=CC=C4C3=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.O.NN>C(O)C>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][NH2:17])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69480980HCID 69480980, compound

Product 1

HCID 552195564-[4-(Trifluoromethyl)phenyl]-1-piperazineethanamineYield 105.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{2-[4-(4-trifluoromethylphenyl)piperazin-1-yl]ethyl}phthalimide (4 g, 9.92 mmol) prepared in Reference Example 153 was suspended in ethanol (30 ml), to which hydrazine monohydrate (0.53 ml, 10.91 mmol) was added, and the mixture was heated under reflux for 5 hours. The reaction mixture was allowed to return to room temperature, and the resulting precipitates were collected by filtration. This was purified by silica gel column chromatography (methylene chloride/ethyl acetate=100/1) to afford 2-[4-(4-trifluoromethylphenyl)piperazin-1-yl]ethylamine (2.87 g, yield 100%) as a colorless crystalline powder.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. customto return to room temperature
  5. customthe resulting precipitates
  6. filtrationwere collected by filtration
  7. customThis was purified by silica gel column chromatography (methylene chloride/ethyl acetate=100/1)

Sources & evidence

ORD record
ord-8883a492042f4c8e8e9a1698d53f31e3
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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