Sodium hydride → N-[2-(4-Morpholinyl)ethyl]-1,2-benzisoxazol-3-amine

HRID 1080421

반응식

HRID 1080421 반응식
[NH2:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[H-].[Na+].Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CO.C(Cl)Cl>CN(C)C=O>[N:16]1([CH2:15][CH2:14][NH:1][C:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[O:4][N:3]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 767274-(2-Chloroethyl)morpholineHCID 27797491,2-Benzoxazol-3-amineHCID 21226129Dichloromethane methanol

생성물 1

HCID 15453430N-[2-(4-Morpholinyl)ethyl]-1,2-benzisoxazol-3-amine수율 38.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 3-amino-1,2-benzisoxazole (3.5 g) in N,N-dimethylformamide (DMF) (100 ml) was added sodium hydride (0.8 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)morpholine (4.0 g) in DMF (50 ml) was added followed by heating to 120° C. for one hour. TLC (5% MeOH/DCM) analysis revealed the absence of starting material. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with water, dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 1.5-2.5% MeOH/DCM afforded the product (2.5 g), m.p. 79°-80° C.

후처리

  1. temperatureby heating to 120° C. for one hour
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. washFlash column chromatography (silica gel) eluting with 1.5-2.5% MeOH/DCM

출처 및 근거

ORD 기록
ord-643a9c38b4584331ba17195005dd8788
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580982

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