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

HRID 1080421

反応式

HRID 1080421 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-643a9c38b4584331ba17195005dd8788
出典データセット
uspto-grants-1996_12
特許番号
US05580982

関連ノート

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