Sodium Bicarbonate → HCID 14837053, 화합물

HRID 2072808노트

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HRID 2072808 반응식
C(=O)(O)[O-].[Na+].[F:6][C:7]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:8]=1[O:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Cl[CH2:25][CH2:26][CH2:27][C:28]1[C:32]2[CH:33]=[C:34]([O:39][CH3:40])[C:35]([O:37][CH3:38])=[CH:36][C:31]=2[O:30][N:29]=1>CN(C)C=O.[I-].[K+]>[CH3:40][O:39][C:34]1[C:35]([O:37][CH3:38])=[CH:36][C:31]2[O:30][N:29]=[C:28]([CH2:27][CH2:26][CH2:25][N:13]3[CH2:14][CH2:15][CH:10]([O:9][C:8]4[C:16]([F:23])=[C:17]([F:22])[C:18]([F:21])=[C:19]([F:20])[C:7]=4[F:6])[CH2:11][CH2:12]3)[C:32]=2[CH:33]=1

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidineHCID 14837050HCID 14837050, 화합물

생성물 1

HCID 14837053HCID 14837053, 화합물수율 60.4%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6228Dimethylformamide용매2회

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온도
70 °C

실험 절차

A mixture of 10 g of sodium bicarbonate, 0.12 g of potassium iodide, 5.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine and 75 ml of dimethylformamide was treated with a solution of 5.37 g of 3-(3-chloropropyl)-5,6-dimethoxy-1,2-benzisoxazole in 25 ml dimethylformamide and stirred for five hours at 70° C. The reaction mixture was filtered and the filtrate poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, evaporation under reduced pressure afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate) to yield 5.5 g of 1-[(5,6-dimethoxy-1,2-benzisoxazol-3-yl)propyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as a waxy solid. This material was dissolved in isopropanol and acidified to pH 1 with etheral hydrogen chloride to precipitate the corresponding hydrochloride salt. Recrystallization from isopropanol afforded 3.3 g (36%) of 1-[(5,6-dimethoxy- 1,2-benzisoxazol-3-yl)propyl]-4-(2,3,4,5, 6-pentafluorophenoxy)piperidine hydrochloride, m.p. 210°-212° C.

후처리

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate poured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. customevaporation under reduced pressure
  8. customafforded a residue which
  9. customwas purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate)

출처 및 근거

ORD 기록
ord-75f2d8b75943487eacc71c0073258941
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04914204

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