Hydrochloric Acid → 4-{2-[(6-Chloro-2-methylpyridin-3-yl)methoxy]ethyl}morpholin-3-one

HRID 385981

반응식

HRID 385981 반응식
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH2:8][C:7]1=[O:12].Br[CH2:14][C:15]1[C:16]([CH3:22])=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=1.Cl>C1COCC1.O>[Cl:21][C:18]1[N:17]=[C:16]([CH3:22])[C:15]([CH2:14][O:3][CH2:4][CH2:5][N:6]2[CH2:11][CH2:10][O:9][CH2:8][C:7]2=[O:12])=[CH:20][CH:19]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 152874004-(2-Hydroxyethyl)morpholin-3-oneHCID 595261743-(Bromomethyl)-6-chloro-2-methylpyridine

생성물 1

HCID 595259664-{2-[(6-Chloro-2-methylpyridin-3-yl)methoxy]ethyl}morpholin-3-one

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Sodium hydride (190 mg of a 60%, 4.76 mmol) was suspended in THF (12.2 mL) and cooled to 0° C. 4-(2-Hydroxyethyl)morpholin-3-one (230 mg, 1.59 mmol) was added and the slurry was stirred for thirty minutes at 0° C. 3-(Bromomethyl)-6-chloro-2-methylpyridine (Example 421 Step 2) (350 mg, 1.59 mmol) was added and the solution was heated to 50° C. overnight. The reaction mixture was then cooled to ambient temperature, diluted with water, acidified using 1 N aqueous hydrochloric acid, and extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, filtered, concentrated, and purified by silica gel chromatography (0-2% methanol in ethyl acetate) to afford the title compound.

후처리

  1. temperaturethe solution was heated to 50° C. overnight
  2. temperatureThe reaction mixture was then cooled to ambient temperature
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (0-2% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-9cc50da4fccd40e0a10e57c7a83005c9
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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