Cyclohexylamine → 3-[2-(4-Cyclohexylpiperazin-1-yl)-2-phenylethyl]phenol

HRID 1679427Notes

Reaction equation

HRID 1679427 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH:9]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1)[CH2:6][CH2:7]Cl.[CH:24]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])O.[Na+]>C(O)C>[CH:24]1([N:30]2[CH2:7][CH2:6][N:5]([CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=3)[CH2:4][CH2:3]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 516892Sodium BicarbonateHCID 213114493-{2-[Bis(2-chloroethyl)amino]-2-phenylethyl}phenol--hydrogen chloride (1/1)

Product 1

HCID 1296313-[2-(4-Cyclohexylpiperazin-1-yl)-2-phenylethyl]phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (60 ml) are dissolved dl-N,N-bis(2-chloroethyl)-1-phenyl-2-(3-hydroxyphenyl)ethylamine hydrochloride (3.7 g) and cyclohexylamine (1.4 g) and thereto is added sodium hydrogen carbonate (3.0 g). The mixture is refluxed with stirring for 24 hours. After the reaction, the solvent is distilled off. The the residue is added a diluted sodium carbonate aqueous solution and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried over anhydrous sodium sulfate, and the solvent is distilled off. The residue (crude free base) is dissolved in a small amount of methanol and the mixture is made acidic with a 25% hydrobromic acid-acetic acid solution and allowed to cool. The precipitated crystals are washed with a mixture of acetone and ether and recrystallized from methanol to give the desired compound as dihydrobromide (2.9 g), melting point: 268°-270° C.

Workup

  1. temperatureThe mixture is refluxed
  2. customAfter the reaction
  3. distillationthe solvent is distilled off
  4. additionThe the residue is added a diluted sodium carbonate aqueous solution
  5. extractionthe mixture is extracted with ethyl acetate
  6. washThe ethyl acetate layer is washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent is distilled off
  9. dissolutionThe residue (crude free base) is dissolved in a small amount of methanol
  10. temperatureto cool
  11. washThe precipitated crystals are washed with a mixture of acetone and ether
  12. customrecrystallized from methanol

Sources & evidence

ORD record
ord-53a1aaf6c8914caabea2ee95f895b097
Source dataset
uspto-grants-1978_03
Patent number
US04080453

Reaction notes

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