Hydrochloric Acid → 3-[4-(3-Chlorophenyl)piperazin-1-yl]propan-1-amine

HRID 373589Notes

Reaction equation

HRID 373589 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.CO>O>[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:13][CH2:14]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19810680HCID 19810680, compound

Product 1

HCID 35067593-[4-(3-Chlorophenyl)piperazin-1-yl]propan-1-amineYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Gaseous hydrochloric acid is introduced for 10 min into a round bottom flask containing 11.2 g (22.6 mmol) of 3-[4-(3-chlorophenyl]piperazin-1-yl]-N-(triphenylmethyl)propanamine and 300 ml of methanol, while the mixture is cooled in a bath of iced water. The mixture is allowed to return to room temperature and is then heated under reflux for 5.5 h. The solution is reduced to half its volume and is allowed to cool. The solid which precipitates is filtered off, is treated with water and aqueous ammonia, the mixture is extracted with ethyl acetate, the organic phase is washed with water and is dried and the solvent is evaporated off. 3.9 g of light yellow oil are obtained.

Workup

  1. customto return to room temperature
  2. temperatureis then heated
  3. temperatureunder reflux for 5.5 h
  4. temperatureto cool
  5. customThe solid which precipitates
  6. filtrationis filtered off
  7. additionis treated with water and aqueous ammonia
  8. extractionthe mixture is extracted with ethyl acetate
  9. washthe organic phase is washed with water
  10. customis dried
  11. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-847f67f3482f4ecda0dd398ff8783271
Source dataset
uspto-grants-1992_11
Patent number
US05164397

Reaction notes

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