Potassium Carbonate → 1-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-piperazine

HRID 2270932Notes

Reaction equation

HRID 2270932 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Cl.Cl[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 891481,4-Benzodioxan-6-ylamineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 10713381-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-piperazineYield 30.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 1,4-benzodioxan-6-amine (2.00 g, 13.2 mmol), bis-(2-choroethyl)amine hydrochloride (3.54 g, 19.8 mmol), and potassium carbonate (1.83 g, 13.2 mmol) in of 20 mL chlorobenzene is heated to reflux for 24 hours. The dark brown reaction mixture is then partitioned between 3N NaOH and methylene chloride. The organic layer is separated, dried over Mg2SO4, filtered and concentrated. Purification by flash column chromatography (8% methanol/methylene chloride on silica) provides 0.88 g (30%) of the desired 1-(1,4-benzodioxan-6-yl)piperazine as a white solid (m.p. 138° C., TLC Rf 0.37 with 10% methanol/methylene chloride).

Workup

  1. temperatureto reflux for 24 hours
  2. customThe dark brown reaction mixture is then partitioned between 3N NaOH and methylene chloride
  3. customThe organic layer is separated
  4. dry with materialdried over Mg2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (8% methanol/methylene chloride on silica)

Sources & evidence

ORD record
ord-04c3165ab2714e039ec942b76df7d713
Source dataset
uspto-grants-2001_12
Patent number
US06333329B2

Reaction notes

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