Potassium Carbonate → 1-(3,4-Dihydro-2H-1-benzopyran-6-yl)piperazine

HRID 567381노트

반응식

HRID 567381 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2.Cl.Cl[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1>[O:8]1[C:9]2[C:4](=[CH:3][C:2]([N:1]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 132978913,4-dihydro-2H-1-benzopyran-6-amine

생성물 1

HCID 154850101-(3,4-Dihydro-2H-1-benzopyran-6-yl)piperazine

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

실험 절차

A solution of 6-aminochroman from part 2 of this example (0.300 g, 2.013 mmol), bis-(2-choroethyl)amine hydrochloride (0.539 g, 3.020 mmol) and potassium carbonate (0.278 g, 2.013 mmol) in 10 mL chlorobenzene is heated at reflux for 24 h . 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 (5% methanol-methylene chloride) affords 0.157 g (36%) of 1-(chroman-6-yl) piperazine as a white solid, TLC Rf 0.35 (elution with 10% methanol-methylene chloride).

후처리

  1. temperatureat reflux for 24 h
  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 (5% methanol-methylene chloride)
  8. customaffords
  9. wash0.157 g (36%) of 1-(chroman-6-yl) piperazine as a white solid, TLC Rf 0.35 (elution with 10% methanol-methylene chloride)

출처 및 근거

ORD 기록
ord-86cf9ea4b08440479b9a51f1466e5f13
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177566B1

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