Benzylamine → HCID 18007303、化合物

HRID 274043ノート

反応式

HRID 274043 の反応式
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=O)[CH2:11][C:5]=2[CH:4]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>O.C([BH3-])#N.[Na+].C(O)(=O)C>[CH2:15]([NH:22][CH:10]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

8

反応物 4

HCID 7504Benzylamine2 回HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 105595743-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-one

生成物 1

HCID 18007303HCID 18007303、化合物

試薬・触媒・溶媒 3

HCID 5003444Sodium cyanoborohydride触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a mixture of 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (3.6 g), benzylamine (2.5 ml), and acetic acid (27 ml) in water bath was added portionwise sodium cyanoborohydride (0.49 g), and the mixture was stirred at ambient temperature for 5 hours. Additional benzylamine (2.5 ml) and sodium cyanoborohydride (0.10 g) were added to the mixture, and stirring was continued for an additional 2 hours. The reaction mixture was made alkaline (pH>8) with 10% sodium hydroxide (150 ml), and extracted once with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; n-hexane-ethyl acetate; 3:1 to 2:1 to 1:1) to give N-benzyl-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (4.8 g) as an oil.

後処理

  1. stirringstirring
  2. waitwas continued for an additional 2 hours
  3. extractionextracted once with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (gradient elution; n-hexane-ethyl acetate; 3:1 to 2:1 to 1:1)

出典と根拠

ORDレコード
ord-0906f7099905489692a4cce3391e5e4a
出典データセット
uspto-grants-1995_02
特許番号
US05387710

反応ノート

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