Sodium Iodide → HCID 69946958, 화합물

HRID 1416927노트

반응식

HRID 1416927 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.C[O:21][C:22](=[O:35])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][C:24]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[OH-].[Na+]>C(O)C.O.C1(C)C=CC=CC=1.CC(=O)CC>[ClH:1].[ClH:1].[CH:16]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]([CH2:4][CH2:3][CH2:2][N:32]3[CH2:33][CH2:34][N:29]([C:24]4[C:23]([C:22]([OH:35])=[O:21])=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:30][CH2:31]3)[C:6]=2[CH:19]=[CH:18][CH:17]=1

참가 물질

10

반응물 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepineHCID 20132428Methyl 2-(piperazin-1-yl)pyridine-3-carboxylate

생성물 1

HCID 69946958HCID 69946958, 화합물수율 50%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

A mixture of 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine (4.54 g, 16.7 mmol), 2-piperazinylnicotinic acid methyl ester 3.7 g, 16.7 mmol), dry potassium carbonate (6.92 g, 50.1 mmol), sodium iodide (2.5 g, 16.7 mmol) and 2-butanone (50 ml) was heated at reflux temperature for 60 h. After cooling to room temperature, toluene (100 ml) and water (100 ml) were added. The organic layer was separated, washed with water (2×50 ml) and evaporated in vacuo. The crude product was purified by column chromatography on silica gel using a mixture of toluene and ethyl acetate (3:1) containing triethylamine (2.5%) as eluent. This afforded 2.3 g (30%) of 2-(4-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-1-piperazinyl)-3-pyridinecarboxylic acid methyl ester as an oil. A mixture of the above ester (2.3 g, 5.04 mmol) dissolved in a mixture of 2 N sodium hydroxide (8.32 ml, 16.63 mmol) and ethanol (25 ml) was stirred at room temperature for 16 h. The ethanol was evaporated in vacuo, and the remainder was diluted with water (50 ml). 2 N Hydrochloric acid (20 ml) was added, and the solution was washed with diethyl ether (25 ml). The aqueous phase was extracted with dichloromethane (3×30 ml). The combined organic extracts were dried (MgSO4) and evaporated in vacuo to afford a foam. This was crystallized from tetrahydrofuran, filtered and dried, affording 1.20 g (50%) of the title compound.

후처리

  1. temperaturewas heated
  2. temperatureat reflux temperature for 60 h
  3. customThe organic layer was separated
  4. washwashed with water (2×50 ml)
  5. customevaporated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel using
  7. additiona mixture of toluene and ethyl acetate (3:1)
  8. additioncontaining triethylamine (2.5%) as eluent
  9. customThe ethanol was evaporated in vacuo
  10. additionthe remainder was diluted with water (50 ml)
  11. addition2 N Hydrochloric acid (20 ml) was added
  12. washthe solution was washed with diethyl ether (25 ml)
  13. extractionThe aqueous phase was extracted with dichloromethane (3×30 ml)
  14. dry with materialThe combined organic extracts were dried (MgSO4)
  15. customevaporated in vacuo
  16. customto afford a foam
  17. customThis was crystallized from tetrahydrofuran
  18. filtrationfiltered
  19. customdried

출처 및 근거

ORD 기록
ord-6aa987ee1abb4a3abe8e3d740b53709e
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05916889

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