Morpholine → 4-(3,5-Dichlorophenyl)morpholine

HRID 1514948

反応式

HRID 1514948 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

7

反応物 4

HCID 8083MorpholineHCID 764241,3-Dichloro-5-iodobenzeneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

生成物 1

HCID 669665754-(3,5-Dichlorophenyl)morpholine

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3,5-dichloroiodobenzene (272 mg, 1 mmol) in anhydrous THF (3 mL) was added morpholine (200 μL, 2 mmol), catalytic (+/−) BINAP (6 mol %), catalytic Pd2(dba)3 (3 mol %) and sodium tert-butoxide (192 mg, 2 mmol). The mixture was sparged with N2 for 5 minutes, then the vial was sealed and heated at 80° C. for 18 h. The reaction mixture was directly purified via flash chromatography on silica gel, eluting with a 0-50% gradient of ethyl acetate/heptane to obtain 4-(3,5-dichlorophenyl)-morpholine as a white solid. 1H NMR (CDCl3, 400 MHz) δ 6.84 (t, J=1.71 Hz, 1H), 6.75 (d, J=1.77 Hz, 2H), 3.81-3.87 (m, 4H), 3.13-3.19 (m, 4H). MS (m/z) 232.2 (M+1).

後処理

  1. customThe mixture was sparged with N2 for 5 minutes
  2. customthe vial was sealed
  3. customThe reaction mixture was directly purified via flash chromatography on silica gel
  4. washeluting with a 0-50% gradient of ethyl acetate/heptane

出典と根拠

ORDレコード
ord-06d580569c1b42948e3f24decc4c70d8
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

関連ノート

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