Hydrochloric Acid → 2-Chloro-4-[4-(3-cyclohexylpropyl)piperazin-1-yl]-phenol hydrochloride

HRID 269882Notes

Reaction equation

HRID 269882 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:17][CH2:16]2)=[CH:11][C:10]=1[Cl:30])C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:30].[Cl:30][C:10]1[CH:11]=[C:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:17][CH2:16]2)[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 231114081-(4-Benzyloxy-3-chlorophenyl)-4-(3-cyclohexylpropyl)piperazine

Product 1

HCID 231114312-Chloro-4-[4-(3-cyclohexylpropyl)piperazin-1-yl]-phenol hydrochlorideYield 143.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(4-Benzyloxy-3-chlorophenyl)-4-(3-cyclohexylpropyl)-piperazine (1.21 g) was suspended in acetic acid (6.0 mL), and to the suspension conc. hydrochloric acid (2.83 mL) was added, followed by 2 hours' heating under reflux. Allowing the system to cool off, the solvent was distilled off under reduced pressure, and the remaining crystals were washed with acetone and dried under reduced pressure at 60° C., to provide 2-chloro-4-[4-(3-cyclohexylpropyl)piperazin-1-yl]-phenol hydrochloride (760 mg).

Workup

  1. temperature' heating
  2. temperatureunder reflux
  3. temperatureto cool off
  4. distillationthe solvent was distilled off under reduced pressure
  5. washthe remaining crystals were washed with acetone
  6. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-467d597228ba4704a7db597383402d9a
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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