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Triethylamine → 4-(4-Fluorophenyl)-1-[3-(5,11-dihydro-7-hydroxy-[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]piperidine-4-ol

HRID 457067
ノート
印刷プレビュー

反応式

HRID 457067 の反応式
Br[CH2:2][CH2:3][CH:4]=[C:5]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[O:9][C:8]2[CH:16]=[CH:17][CH:18]=[C:19]([OH:20])[C:7]=2[CH2:6]1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2([OH:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1.C(N(CC)CC)C>CN(C=O)C>[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2([OH:34])[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH:4]=[C:5]3[C:15]4[C:10](=[N:11][CH:12]=[CH:13][CH:14]=4)[O:9][C:8]4[CH:16]=[CH:17][CH:18]=[C:19]([OH:20])[C:7]=4[CH2:6]3)[CH2:32][CH2:33]2)=[CH:24][CH:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 774974-(4-Fluorophenyl)piperidin-4-olHCID 667582405-(3-Bromopropylidene)-5,11-dihydro-7-hydroxy-[1]benzoxepino[2,3-b]pyridine

生成物 1

HCID 667581834-(4-Fluorophenyl)-1-[3-(5,11-dihydro-7-hydroxy-[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]piperidine-4-ol収率 39%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a solution of 5-(3-bromopropylidene)-5,11-dihydro-7-hydroxy-[1]benzoxepino[2,3-b]pyridine (2.59 g) in DMF (10 ml) was added 4-(4-Fluorophenyl)-4-hydroxypiperidine (1.02 g) and triethylamine (835 μM). The solution was stirred at room temperature for 23 hours. The reaction was quenched with water, extracted with ethyl acetate, and evaporated in vacuo. The residue was purified by silica gel chromatography (87:10:3 ethyl acetate: methanol:triethylamine) to yield 0.9 g (39%) of the title compound. 1H-NMR (DMSO) d: 1.64–1.69 (2H, m), 1.74–1.85 (2H, m), 2.27–2.52 (8H, m), 4.81 (1H, s), 5.16 (2H, brs), 6.08 (1H, t), 6.62–6.71 (3H, m), 7.12 (2H, t), 7.40–7.51 (3H, m), 7.72 (1H, dd), 8.48 (1H, dd), 9.09 (1H, s). ESI-MS m/z: 447 (M+1).

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel chromatography (87:10:3 ethyl acetate: methanol:triethylamine)

出典と根拠

ORDレコード
ord-d8744e0f8de34466a8d0fe35d79322e3
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07186729B2

反応ノート

読み込み中…

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