Sodium Hydroxide → 2H-benzazepine

HRID 2421474ノート

反応式

HRID 2421474 の反応式
N1([C:7]2[CH:17]=[CH:16][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][NH:15][C:9]=3[CH:8]=2)CCOCC1.[OH-].[Na+]>CO>[N:15]1[CH2:14][CH:13]=[CH:12][CH:11]=[C:10]2[CH:16]=[CH:17][CH:7]=[CH:8][C:9]=12

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 669638998-Morpholinobenzazepine

生成物 1

HCID 866101862H-benzazepine収率 192.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of the N-acetyl benzazepine (0.14 g, 0.40 mmol) from step I above in methanol (10 mL) was added an aqueous 2N solution of sodium hydroxide (10 mL). The reaction solution was heated under reflux for 72 hours and then cooled to room temperature. The resultant reaction mixture was extracted with dichloromethane, washed with water and aqueous saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The residue obtained was purified by flash column chromatography (dichloromethane to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide) to give the desired 2H-benzazepine (0.11 g, 89%) as a white foam: 1H NMR (DMSO-d6, 500 MHz) δ 7.35 (t, J=7.5 Hz, 2H), 7.24 (t, J=7.5 Hz, 1H), 7.14 (d, J=7.5 Hz, 2H), 6.84 (d, J=2.5 Hz, 1H), 6.65-6.60 (m, 1H), 6.49-6.38 (br, 1H), 4.33 (d, J=8.5 Hz, 1H), 3.95 (d, J=14.5 Hz, 1H), 3.77 (d, J=14.5 Hz, 1H), 3.71 (t, J=5.0 Hz, 4H), 3.10-2.87 (m, 6H), 2.21-2.12 (m, 1H), 2.03-1.85 (m, 1H).

後処理

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 72 hours
  3. customThe resultant reaction mixture
  4. extractionwas extracted with dichloromethane
  5. washwashed with water and aqueous saturated sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue obtained
  9. customwas purified by flash column chromatography (dichloromethane to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide)

出典と根拠

ORDレコード
ord-596eef0a00044048a1a05b1cda8fcad9
出典データセット
uspto-grants-2011_06
特許番号
US07956050B2

反応ノート

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