Acetic Acid → (2-(4-((6-Quinolylamino)methyl)phenoxy)ethyl)diethylamine

HRID 353596

반응식

HRID 353596 반응식
[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[CH3:2].[NH2:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[N:24]1[C:25]2[C:20](=[CH:19][C:18]([NH:17][CH2:11][C:10]3[CH:13]=[CH:14][C:7]([O:6][CH2:5][CH2:4][N:3]([CH2:15][CH3:16])[CH2:1][CH3:2])=[CH:8][CH:9]=3)=[CH:27][CH:26]=2)[CH:21]=[CH:22][CH:23]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 113736-AminoquinolineHCID 14798Sodium HydroxideHCID 4116744-(2-(Diethylamino)-Ethoxy)-BenzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 23514383(2-(4-((6-Quinolylamino)methyl)phenoxy)ethyl)diethylamine수율 8.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a stirred solution of 1.0 gram (0.0045 mole) of 4-(2-(diethylamino)ethoxy)benzaldehyde and 0.65 gram (0.0045 mole) of 6-aminoquinoline (available from Aldrich Chemical Company) in 25 mL of 1,2-dichloroethane (DCE, available from Aldrich Chemical Company) was added 0.3 mL (0.0045 mole) of glacial acetic acid (available from J. T. Baker Inc.) followed by 1.4 grams (0.0068 mole) of sodium triacetoxyborohydride (available from Aldrich Chemical Company). Upon completion of addition, the reaction mixture was stirred at ambient temperature for three hours. At the conclusion of this period, 50 mL of 10% aqueous sodium hydroxide was added dropwise. The resulting solution was extracted with three 25 mL portions of diethyl ether. The extracts were combined, washed with one 25 mL portion of an aqueous solution saturated with sodium chloride, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 1.25 grams of a dark brown paste. The dark brown paste was purified by column chromatography on silica gel, yielding 0.13 gram of Compound 15. The NMR spectrum was consistent with the proposed structure.

후처리

  1. additionUpon completion of addition
  2. extractionThe resulting solution was extracted with three 25 mL portions of diethyl ether
  3. washwashed with one 25 mL portion of an aqueous solution saturated with sodium chloride
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customyielding 1.25 grams of a dark brown paste
  8. customThe dark brown paste was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-fcbe1e5a9d5b42bea75a6652b652f34a
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06753429B2

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