Hydrazine hydrate (1:1) → 8-Methoxy-3-(2-methoxyethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-amine

HRID 1040742ノート

反応式

HRID 1040742 の反応式
[CH3:1][O:2][C:3]1[C:17]([N+:18]([O-])=O)=[CH:16][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][O:14][CH3:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1.O.NN>[Pd].CO>[CH3:1][O:2][C:3]1[C:17]([NH2:18])=[CH:16][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][O:14][CH3:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 67263598HCID 67263598、化合物

生成物 1

HCID 574161508-Methoxy-3-(2-methoxyethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-amine収率 93.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

Into a 1-neck round-bottom flask was added 7-methoxy-3-(2-methoxy-ethyl)-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (2.4 g, 8.56 mmol), hydrazine monohydrate (20 mL, 0.4 mol), and palladium on carbon (10% wt, 50% wet; 400 mg), in methanol (80 mL). The reaction mixture was heated at 70° C. for 3 hours. The reaction mixture was filtered through Celite and was concentrated. The residue was partitioned between diluted NaHCO3 and ethyl acetate. The aqueous phase was extracted with another portion of ethyl acetate, dried (MgSO4), and concentrated to afford 8-methoxy-3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine (2.00 g, 93%). 1H-NMR (CDCl3) δ 6.55 (s, 1H), 6.49 (s, 1H), 3.81 (s, 3H), 3.63 (br s, 2H), 3.53 (t, J=5.8 Hz, 2H), 3.36 (s, 3H), 2.60-2.90 (m, 10H); LC/MS (ESI+): 251.10 (M+H).

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationwas concentrated
  3. customThe residue was partitioned between diluted NaHCO3 and ethyl acetate
  4. extractionThe aqueous phase was extracted with another portion of ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c01825fe0789422696dce958cdec92d8
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

反応ノート

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