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Potassium Iodide → rel-1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone

HRID 1876771
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HRID 1876771 반응식
[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C@H:12]4[CH:17]=[N:16][CH2:15][CH2:14][C@@H:13]4[N:5]([C:6]=23)[CH2:4][CH2:3]1.Cl[CH2:19][CH2:20][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:23].C(N(CC)CC)C.[I-].[K+]>O1CCOCC1.C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C@@H:12]4[CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]([C:24]5[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=5)=[O:23])[CH2:15][CH2:14][C@@H:13]4[N:5]([C:6]=23)[CH2:4][CH2:3]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 68591394HCID 68591394, 화합물

생성물 1

HCID 21302490rel-1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 312751,4-Dioxane용매

실험 절차

A suspension of (6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido-[3′,4′:4,5]-pyrrolo[1,2,3-de]quinoxaline (ca. 11.8 g, ca. 50 mmol), 4-chloro-4′-fluorobutyrophenone (15.0 g, 74.8 mmol), triethylamine (30 mL, 214 mmol), and potassium iodide (12.6 g, 76 mmol) in dioxane (65 ml) and toluene (65 ml) is heated to reflux for 7 hours. After filtration and evaporation of the solvent, 200 ml of DCM is added. The DCM solution is washed with brine, dried (Na2SO4) and concentrated to approximately 55 ml. The concentrated solution is added dropwise to 600 ml of 0.5N HCl ether solution. The solid is filtered off and washed with ether and then dissolved in water. The resulting aqueous solution is basified with 2N NaOH and extracted with DCM. The DCM layers are combined, washed with brine (2×200 mL) and dried (Na2SO4). Evaporation of the solvent and chromatography of the residue over silica gel gives 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido-[3′,4′:4,5]-pyrrolo[1,2,3-de]quinoxalin-8-(7H)-yl)-1-(4-fluorophenyl)-1-butanone.

후처리

  1. temperatureis heated
  2. temperatureto reflux for 7 hours
  3. filtrationAfter filtration and evaporation of the solvent, 200 ml of DCM
  4. additionis added
  5. washThe DCM solution is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to approximately 55 ml
  8. additionThe concentrated solution is added dropwise to 600 ml of 0.5N HCl ether solution
  9. filtrationThe solid is filtered off
  10. washwashed with ether
  11. dissolutiondissolved in water
  12. extractionextracted with DCM
  13. washwashed with brine (2×200 mL)
  14. dry with materialdried (Na2SO4)
  15. customEvaporation of the solvent and chromatography of the residue over silica gel

출처 및 근거

ORD 기록
ord-ba15f9a6669b4bbcbbe677db18b01d27
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08309722B2

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