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

HRID 849495Notes

Reaction equation

HRID 849495 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) δ 3.05, 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-0f5db6370f2a4758a7f3d668994a55d1
Source dataset
uspto-grants-2000_01
Patent number
US06013654

Reaction notes

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