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Benzylamine → N-Benzyl-3-[4-(2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionamide

HRID 220892
ノート
印刷プレビュー

反応式

HRID 220892 の反応式
[N:1]1([C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22](O)=[O:23])=[CH:16][CH:15]=2)=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.S(Cl)(Cl)=O.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>ClCCl>[CH2:29]([NH:36][C:22](=[O:23])[CH2:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]([N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][C:11]3[CH:10]=[CH:9][CH:8]=[CH:3][C:2]2=3)=[O:13])=[CH:19][CH:18]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 575553343-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic Acid

生成物 1

HCID 57555288N-Benzyl-3-[4-(2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionamide収率 50%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A mixture of 3-[4-(2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic acid from Example E65.4 (57 mg, 0.18 mmol) and thionyl chloride (0.2 ml, 2.74 mmol) in dichloromethane (6 ml) was heated at reflux for 2 h then volatiles were removed in vacuo. The residue was dissolved in dichloromethane (8 ml) then benzylamine (0.022 ml, 0.20 mmol) and triethylamine (0.05 ml, 0.36 mmol) were added. The mixture was stirred for 3 h at room temperature then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 30% pet. ether:70% EtOAc) to give a white fluffy solid identified as the title compound (36.5 mg, 50%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customwere removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (8 ml)
  5. concentrationthen concentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant; 30% pet. ether:70% EtOAc)
  7. customto give a white fluffy solid

出典と根拠

ORDレコード
ord-e43d39b8aa4f445f9908714ec0fef785
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202858B2

反応ノート

読み込み中…

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