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

HRID 1018935노트

반응식

HRID 1018935 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f81ab7524ffd4ddbb6e4f91f8c423654
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486164B2

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