Sodium Iodide → HCID 10072481、化合物

HRID 2103737ノート

反応式

HRID 2103737 の反応式
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].Cl.[CH3:29][N:30]([CH3:35])[CH2:31][CH2:32][CH2:33]Cl.[I-].[Na+].C(N(CC)CC)C>C(#N)C>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4](=[O:25])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:12]2[CH2:17][CH2:16][N:15]([CH2:33][CH2:32][CH2:31][N:30]([CH3:35])[CH3:29])[CH2:14][CH2:13]2)=[CH:9][CH:10]=1)[CH3:27]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 10406550HCID 10406550、化合物2 回

生成物 1

HCID 10072481HCID 10072481、化合物収率 25.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of N,N-diethyl-4-[benzyl(piperidin-4-yl)amino]benzamide (Compound 8) (0.29 g, 0.793 mmole) in 25 mL of acetonitrile was added 3-(dimethylamino)propyl chloride hydrochloride (0.013 g, 0.793 mmol), sodium iodide (0.02 g, 0.119 mmol), and triethylamine (0.32 g, 3.18 mmol). The reaction mixture was refluxed for 20 hours under Argon and then was cooled and concentrated in vacuo. To the residue was added, aqueous sodium hydroxide (1 N) solution (30 mL), and the resulting solution was extracted three times with chloroform (25 mL). The organic extracts were combined, washed with sodium carbonate solution, dried (Na2SO4), and concentrated to provide a brown oil. This material was purified on a flash silica gel column (10% methanol-chloroform to 17.5% methanol-chloroform) to provide 0.09 g (25%) of N,N-diethyl-4-[benzyl(1-(3-dimethylaminopropyl)piperidin-4-yl)amino]benzamide as a pale rose glass. MS (ES), m/z 451 (MH+). 300 MHz 1H NMR (CDCl3) δ1.17 (t, J=7.0 Hz, 6H), 1.69-1.89 (m, 4H), 2.14 (br t, 2H), 2.18-2.38 (br m, 2H), 2.42 (s, 4H), 2.47 (t, J=7.1 Hz, 2H), 2.59 (t, J=6.9 Hz, 2H), 3.06 (br d, J=11.6 Hz, 2H), 3.30-3.49 (m, 4H), 3.72-3.90 (br m, 1H), 4.52 (s, 2H), 6.65 (d, J=8.7 Hz, 2H), 7.10-7.30 (m, 7H).

後処理

  1. temperatureThe reaction mixture was refluxed for 20 hours under Argon
  2. temperaturewas cooled
  3. concentrationconcentrated in vacuo
  4. additionTo the residue was added
  5. extractionaqueous sodium hydroxide (1 N) solution (30 mL), and the resulting solution was extracted three times with chloroform (25 mL)
  6. washwashed with sodium carbonate solution
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto provide a brown oil
  10. customThis material was purified on a flash silica gel column (10% methanol-chloroform to 17.5% methanol-chloroform)

出典と根拠

ORDレコード
ord-90c581a46bdd42518b9f61bb415642d2
出典データセット
uspto-grants-2009_08
特許番号
US07576105B2

反応ノート

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