Potassium Iodide → N-[2-(7-Methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide

HRID 1040749

反応式

HRID 1040749 の反応式
[CH3:1][O:2][C:3]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.Cl[CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[CH3:1][O:2][C:3]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:6]2[CH2:7][CH2:8][N:9]([CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[CH2:10][CH2:11][C:5]=2[CH:4]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 81815N-(2-Chloroethyl)acetamideHCID 672643517-Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

生成物 1

HCID 67264615N-[2-(7-Methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide収率 15%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

Into a 1-neck round-bottom flask was added 7-methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.5 g, 2.20 mmol), N-(2-chloro-ethyl)-acetamide (0.45 mL, 4.41 mmol), potassium iodide (92 mg, 0.55 mmol), and potassium carbonate (900 mg, 7 mmol), in N-methylpyrrolidinone (5 mL), and the reaction was heated at 90 overnight. The reaction mixture was next partitioned between water and ethyl acetate, and the layers separated. The aqueous phase was extracted twice with ethyl acetate and the combined organic extracts were washed with water, dried (MgSO4), filtered, and concentrated, and the product was isolated by flash chromatography on SiO2 (MeOH/dichloromethane 0-20%) to give N-[2-(7-Methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide (100 mg, 15%). 1H-NMR (CDCl3) δ 7.67 (s, 1H), 6.84 (s, 1H), 6.11 (br s, 1H), 3.94 (s, 3H), 3.38 (m, 2H), 2.95 (m, 2H), 2.89 (m, 2H), 2.66 (m, 6H), 2.01 (s, 3H); LC/MS (ESI+): 308.02 (M+H).

後処理

  1. customThe reaction mixture was next partitioned between water and ethyl acetate
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe product was isolated by flash chromatography on SiO2 (MeOH/dichloromethane 0-20%)

出典と根拠

ORDレコード
ord-3624346274024ab6947dd84aba3fe65a
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

関連ノート

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