Potassium Carbonate → 1-(3,5-Dichloro-4-methoxyphenyl)piperazine hydrochloride

HRID 1390620Notes

Reaction equation

HRID 1390620 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:11])[C:8]=1[O:9][CH3:10])[NH2:5].Cl.Cl[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:6]=[C:7]([Cl:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 131786513,5-Dichloro-4-methoxyaniline

Product 1

HCID 447171491-(3,5-Dichloro-4-methoxyphenyl)piperazine hydrochlorideYield 29.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3,5-dichloro-4-methoxyaniline (16.0g) and bis-(2-chloroethyl)amine hydrochloride (14.77g) in n-butanol (100 ml) was stirred under reflux for 48 hr. Anhydrous potassium carbonate (11.45g) was added and the resulting mixture was stirred under reflux for a further 24 hr., then filtered hot. The solid which precipitated on cooling was crystallised from ethanol-ether to give 1-(3,5-dichloro-4-methoxyphenyl)piperazine hydrochloride (3.7g) m.p. 252°-255°.

Workup

  1. temperatureunder reflux for 48 hr
  2. stirringthe resulting mixture was stirred
  3. temperatureunder reflux for a further 24 hr
  4. filtration, then filtered hot
  5. customThe solid which precipitated
  6. temperatureon cooling
  7. customwas crystallised from ethanol-ether

Sources & evidence

ORD record
ord-43761a5cadbb4e049c5a8b64a38dc3d6
Source dataset
uspto-grants-1979_02
Patent number
US04139621

Reaction notes

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