Sodium Iodide → 6-[6-(4-hydroxypiperidinyl)hexoxy]-3-methoxy-4H-1-benzopyran-4-one

HRID 1708726노트

반응식

HRID 1708726 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH:16]=[C:15]([O:18][CH3:19])[C:14](=[O:20])[C:13]=2[CH:21]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[OH:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>CC(=O)CC>[OH:30][CH:31]1[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH:16]=[C:15]([O:18][CH3:19])[C:14](=[O:20])[C:13]=3[CH:21]=2)[CH2:33][CH2:32]1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 189596986-(6-chlorohexoxy)-3-methoxy-4H-1-benzopyran-4-one

생성물 1

HCID 189597226-[6-(4-hydroxypiperidinyl)hexoxy]-3-methoxy-4H-1-benzopyran-4-one수율 82.8%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

A mixture of 2 g of 6-(6-chlorohexoxy)-3-methoxy-4H-1-benzopyran-4-one, 1 g of sodium iodide, 0.6 g of potassium carbonate, and 1.4 g of 4-hydroxypiperidine was refluxed in butanone for 96 hours. The solvent was removed and the residue stirred with ethyl acetate and filtered. The solution was washed with water and then dried over sodium sulfate. The solvent was removed to give an oil which was chromatographed over silica gel to give 2 g of 6-[6-(4-hydroxypiperidinyl)hexoxy]-3-methoxy-4H-1-benzopyran-4-one which was converted to the hydrochloride salt by dissolving in ethyl acetate and adding 1 N ethereal HCL: mp 124°-125° C.

후처리

  1. customThe solvent was removed
  2. filtrationfiltered
  3. washThe solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. customto give an oil which
  7. customwas chromatographed over silica gel

출처 및 근거

ORD 기록
ord-a3340a678afa462e8e8b70bcef5e8e5c
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05359098

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