Potassium Carbonate → 1-(3-Chloro-4-methoxyphenyl)piperazine

HRID 1416294Notes

Reaction equation

HRID 1416294 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[O:5][CH3:6].[ClH:11].Cl[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]Cl.C(=O)([O-])[O-].[K+].[K+].O.C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C(=O)C>[Cl:11][C:3]1[CH:2]=[C:9]([N:10]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][C:4]=1[O:5][CH3:6]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 4074322-Chloro-4-methoxyanilineHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 86585896Sodium bicarbonate water

Product 1

HCID 47395621-(3-Chloro-4-methoxyphenyl)piperazineYield 32.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-chloro-4-anisidine (Aldrich; 0.633 g), bis(2-chloroethyl)amine hydrochloride (Aldrich; 0.860 g), potassium carbonate (1.11 g), and N,N-dimethylacetamide (6 mL) is stirred at 100° C. for 17.5 h, at which time the mixture is cooled and partioned between dichloromethane and water/sodium bicarbonate. The organic layers are dried over sodium sulfate, concentrated, and the residue is chromatographed on silica gel using methanol/dichloromethane (8/92) to give 0.297 g of 1-(3-chloro-4-methoxyphenyl)piperazine. 1H NMR (CDCl3) δ3.05, 3.86, 6.80, 6.87, 6.99.

Workup

  1. temperatureis cooled
  2. dry with materialThe organic layers are dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-e66c4b046a254884acf15bca64dc9962
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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