Hydrochloric Acid → 2-[4-(3,4-Dichloro-benzyl)-morpholin-2-ylmethyl]-isoindole-1,3-dione

HRID 1371400노트

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HRID 1371400 반응식
[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[Cl:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:20][NH:21][CH2:22]CO.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.Cl>O1CCCC1.C(OCC)(=O)C>[Cl:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:20][N:21]1[CH2:29][CH2:3][O:1][CH:2]([CH2:4][N:5]2[C:6](=[O:15])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]2=[O:14])[CH2:22]1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2605252-[[(3,4-Dichlorophenyl)methyl]amino]ethanol

생성물 1

HCID 219628802-[4-(3,4-Dichloro-benzyl)-morpholin-2-ylmethyl]-isoindole-1,3-dione

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
66 °C

실험 절차

To a solution of 2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-dione (N-(2,3-epoxypropyl)phthalimide) (2 g) in tetrahydrofuran (4 ml) was added 2-[(3,4-dichlorobenzyl)amino]ethanol (2.16 g) with stirring, under a nitrogen atmosphere. The mixture was heated to 66° C. for 22 h, then cooled to 0° C. A further portion of tetrahydrofuran (10 ml) was added, followed by triphenylphosphine (2.88 g). Diisopropyl azodicarboxylate (2.2 g) was then added over 10 min. The mixture was stirred at 0° C. for a further 30 min, and at room temperature for 14 h. To the crude solution was added ethyl acetate (100 ml), then 2M aqueous hydrochloric acid (250 ml). The resulting white precipitate was isolated by filtration, and dried in vacuo to give the title compound as its white crystalline hydrochoride salt (2.01 g). This was partitioned between 8% aqueous sodium bicarbonate (200 ml) and ethyl acetate (50 ml). The organic phase was separated, dried over magnesium sulfate and the solvent evaporated in vacuo to give a solid. Dichloromethane (20 ml) was added to the residue and the solvent again evaporated in vacuo to give the title compound as a white solid (1.1 g).

후처리

  1. temperaturecooled to 0° C
  2. stirringThe mixture was stirred at 0° C. for a further 30 min
  3. customThe resulting white precipitate was isolated by filtration
  4. customdried in vacuo

출처 및 근거

ORD 기록
ord-6644755d7b44498a95ebd04d4b677bbd
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157457B2

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