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

HRID 567380Notes

Reaction equation

HRID 567380 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-3de786b878814078a1e34ef1aa47d1cf
Source dataset
uspto-grants-2001_01
Patent number
US06177566B1

Reaction notes

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