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

HRID 1679426Notes

Reaction equation

HRID 1679426 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].Cl.Cl[CH2:15][CH2:16][N:17]([CH:21]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29])[CH2:18][CH2:19]Cl>C(O)C>[CH:1]1([N:7]2[CH2:15][CH2:16][N:17]([CH:21]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[OH:29])[CH2:18][CH2:19]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 516892Sodium BicarbonateHCID 203969342-{2-[Bis(2-chloroethyl)amino]-2-phenylethyl}phenol--hydrogen chloride (1/1)

Product 1

HCID 124669182-[2-(4-Cyclohexylpiperazin-1-yl)-2-phenylethyl]phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (30 ml) are dissolved in N,N-bis(2-chloroethyl)-1-phenyl-2-(2-hydroxyphenyl)ethylamine hydrochloride (1.9 g) and cyclohexylamine (0.7 g) and thereto is added sodium hydrogen carbonate (1.4 g). The mixture is refluxed with stirring for 24 hours. After the reaction, the solvent is distilled off. To the residue is added a diluted aqueous ammonia and the alkaline solution is extracted with chloroform. The chloroform layer is washed with water, dried over anhydrous sodium sulfate, and the solvent is distilled off. The crystalline residue (crude free base) is dissolved in a small amount of ethanol and thereto is added a 25% hydrobromic acid-acetic acid solution and the mixture is allowed to cool. The precipitated crystals are recrystallized from ethanol to give the desired compound as dihydrobromide (1.4 g), melting point: 245.5°-247.5° C.

Workup

  1. temperatureThe mixture is refluxed
  2. customAfter the reaction
  3. distillationthe solvent is distilled off
  4. additionTo the residue is added a diluted aqueous ammonia
  5. extractionthe alkaline solution is extracted with chloroform
  6. washThe chloroform layer is washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent is distilled off
  9. dissolutionThe crystalline residue (crude free base) is dissolved in a small amount of ethanol
  10. additionis added a 25% hydrobromic acid-acetic acid solution
  11. temperatureto cool
  12. customThe precipitated crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-7e2f4a8db1414bdbaa83fbe9006fc67f
Source dataset
uspto-grants-1978_03
Patent number
US04080453

Reaction notes

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