Benzylamine → Benzyl-(3-methoxy-4-nitro-benzyl)amine

HRID 1019752ノート

反応式

HRID 1019752 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([O:12][CH3:13])[CH:4]=1.C(N(CC)CC)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([NH:28][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([O:12][CH3:13])[CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 126216043-Methoxy-4-nitrobenzyl bromide

生成物 1

HCID 22046378Benzyl-(3-methoxy-4-nitro-benzyl)amine収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(bromomethyl)-2-methoxy-1-nitrobenzene (1.0 g, 4.06 mmol) in THF (15 ml), triethylamine (1.23 g, 12.19 mmol) and benzyl amine (1.3 g, 12.19 mmol) were added at RT and the reaction was stirred for 2 hours. The reaction mixture was partitioned between water (50 ml) and EtOAc (25 ml) and the separated aqueous layer was extracted with EtOAc (15 ml). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane to give the title compound (1.0 g, 91%).

後処理

  1. customThe reaction mixture was partitioned between water (50 ml) and EtOAc (25 ml)
  2. extractionthe separated aqueous layer was extracted with EtOAc (15 ml)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane

出典と根拠

ORDレコード
ord-34f6a77ac2c04cc8a2edee44b28081cc
出典データセット
uspto-grants-2014_05
特許番号
US08716287B2

反応ノート

読み込み中…