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Triethylamine → HCID 16755443、化合物

HRID 1727385
ノート
印刷プレビュー

反応式

HRID 1727385 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([C:13]([O-])=[O:14])[N:10]=[C:9]2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.[Li+].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:36]2[CH:37]=[CH:38][CH:39]=C[C:35]=2[N:34]=[N:33]1.NN1CCCCC1.C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([C:13]([NH:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:14])[N:10]=[C:9]2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=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 8471TriethylamineHCID 166581-AminopiperidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23704465HCID 23704465、化合物

生成物 1

HCID 16755443HCID 16755443、化合物収率 31.2%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

Part B: A mixture of the crude lithium 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-4,5-dihydro-1H-imidazole-4-carboxylate (1.0 gram, ˜0.0027 mol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (1.2 gram, 0.0027 mol), 1-aminopiperidine (0.3 gram, 0.003 mol) and triethylamine (1 ml) in DMF (30 ml) is stirred at room temperature for 16 hours. After concentration in vacuo, water is added and the resulting mixture is extracted (2×) with dichloromethane. The dichloromethane layers are collected, dried over MgSO4, filtered and concentrated in vacuo to give a residue that is further purified by flash chromatography (silicagel, dichloromethane/methanol=95/5 (v/v)) to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-imidazole-4-carboxamide (380 mg, 31% yield). Melting point: 113-116° C. 1H-NMR (200 MHz, CDCl3): δ 1.33-1.48 (m, 2H), 1.60-1.80 (m, 4H), 2.68-2.82 (m, 4H), 4.28-4.35 (m, 2H), 4.84 (dd, J=11 and 9 Hz, 1H), 6.65 (br d, J=8 Hz, 2H), 7.11 (br d, J=8 Hz, 2H), 7.23-7.33 (m, 2H), 7.41 (d, J=2 Hz, 1H), 7.57 (br s, 1H).

後処理

  1. concentrationAfter concentration in vacuo, water
  2. additionis added
  3. extractionthe resulting mixture is extracted (2×) with dichloromethane
  4. customThe dichloromethane layers are collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue that
  9. customis further purified by flash chromatography (silicagel, dichloromethane/methanol=95/5 (v/v))

出典と根拠

ORDレコード
ord-be8e5c2f8d3c4f8dba9b7a4e1fa4d800
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07495108B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート