Water → (4-Benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine

HRID 479808ノート

反応式

HRID 479808 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].[CH2:10]([N:17]1[CH2:23][CH2:22][CH2:21][O:20][CH:19]([CH2:24]Cl)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(O)CCC.C(Cl)Cl>[CH2:10]([N:17]1[CH2:23][CH2:22][CH2:21][O:20][CH:19]([CH2:24][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

7

反応物 4

HCID 962WaterHCID 5238Sodium IodideHCID 6115AnilineHCID 103993654-Benzyl-2-(chloromethyl)-1,4-oxazepane

生成物 1

HCID 21904409(4-Benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
110 °C

実験手順

Aniline (2.59 mL, 28.4 mmol) and NaI (4.06 g, 27.1 mmol) were added to a solution of 4-benzyl-2-chloromethyl-1,4-oxazepane (79) (6.49 g, 27.1 mmol) in n-butanol (68 mL, 0.4 M), and the reaction was heated to 110° C. until the reaction was judged complete by TLC (4 h). The reaction was cooled to room temperature, and water and CH2Cl2 were added. The organic layer was removed, and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to achieve (4-benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine 80, which was used without purification in the next reaction. 1H NMR (partial, CDCl3) 4.08-3.86 (3H, m), 3.80 (1H, d, J=13.3 Hz), 3.73 (1H, d, J=13.3 Hz), 3.22-3.05 (2H, m), 2.95-2.70 (3H, m), 2.64 (1H, dd, J=13.6, 7.6 Hz), 2.1-1.9 (2H, m) ppm. 13C NMR (CDCl3) 148.33, 139.38, 129.28, 129.11, 128.46, 127.23, 117.44, 113.13, 76.70, 67.49, 62.92, 59.35, 54.76, 46.93, 30.75 ppm. LRMS: 296.68.

後処理

  1. customwas judged complete by TLC (4 h)
  2. temperatureThe reaction was cooled to room temperature
  3. customThe organic layer was removed
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customwas used without purification in the next reaction

出典と根拠

ORDレコード
ord-a7d04b699be94bb4a7df58dbfb380e88
出典データセット
uspto-grants-2003_11
特許番号
US06645980B1

反応ノート

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