1,10-Phenanthroline → N-(3-morpholin-4-yl-phenyl)-hydrazinecarboxylic acid tert-butyl ester

HRID 600999

反応式

HRID 600999 の反応式
I[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:14]([O:18][C:19](=[O:22])[NH:20][NH2:21])([CH3:17])([CH3:16])[CH3:15].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu]I.O>[C:14]([O:18][C:19]([N:20]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:3]=1)[NH2:21])=[O:22])([CH3:17])([CH3:16])[CH3:15]

参加物

8

反応物 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 70091tert-Butyl carbazateHCID 545364344-(3-Iodophenyl)morpholine

生成物 1

HCID 58977018N-(3-morpholin-4-yl-phenyl)-hydrazinecarboxylic acid tert-butyl ester収率 62.1%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-(3-iodo-phenyl)-morpholine (1.81 g, 6.26 mmol) in DMF (6.5 mL) under nitrogen was added tert-butylcarbazate (993 mg, 7.52 mmol), copper (I) iodide (59.5 mg, 0.313 mmol), 1,10-phenanthroline (113 mg, 0.626 mmol) and cesium carbonate (2.85 g, 8.77 mmol). The mixture was heated at 80° C. for 18 h and then cooled to room temperature. Water (100 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated. The residue was purified by silica gel column chromatograghy eluted with EtOAc:hexanes (25 to 50% EtOAc) to give N-(3-morpholin-4-yl-phenyl)-hydrazinecarboxylic acid tert-butyl ester (1.14 g, 62%) as a yellowi oil. MS (ES+): m/z=294.2. 1H NMR (DMSO-d6, 500 MHz): δ 1.44 (s, 9H), 3.06 (t, 4H), 3.73 (t, 4H), 4.97 (s, 2H), 6.66 (dd, 1H), 6.91 (d, 1H), 7.01-7.05 (m, 1H), 7.09-7.14 (m, 1H).

後処理

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatograghy
  6. washeluted with EtOAc

出典と根拠

ORDレコード
ord-5fbda8b809dd43cf9868a0ec889ba50f
出典データセット
uspto-grants-2011_03
特許番号
US07902239B2

関連ノート

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