Allyl bromide → HCID 10319122、化合物

HRID 2103734ノート

反応式

HRID 2103734 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].C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[CH:35]=[CH2:36]>C(#N)C.O>[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]([CH2:36][CH:35]=[CH2:34])[CH2:14][CH2:13]2)=[CH:9][CH:10]=1)[CH3:27]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 10406550HCID 10406550、化合物2 回

生成物 1

HCID 10319122HCID 10319122、化合物収率 40%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of N,N-diethyl-4-[benzyl(piperidin-4-yl)amino]benzamide (Compound 8) (0.25 g, 0.684 mmole) in 10 mL of acetonitrile was added potassium carbonate (0.10 g, 0.752 mmole) and allyl bromide (0.08 g, 0.684 mmol). The reaction mixture was stirred for six days under Argon and then was diluted with water (50 mL). This solution was extracted three times with dichloromethane (50 mL). The organic extracts were combined, washed with sodium carbonate solution, dried (Na2SO4), and concentrated to provide a yellow foam. This material was purified on a flash silica gel column (5% methanol-chloroform to 10% methanol-chloroform) to provide 0.11 g (40%) of N,N-diethyl-4-[benzyl(1-allylpiperidin-4-yl)amino]benzamide as a colorless oil. MS (ES), m/z 406 (MH+). 300 MHz 1H NMR (CDCl3) δ1.17 (t, J=7.0 Hz, 6H), 1.68-1.90 (m, 4H), 2.06 (br t, J=10.6 Hz, 2H), 2.91-3.08 (m, 4H), 3.31-3.52 (m, 4H), 3.75-3.92 (br m, 1H), 4.52 (s, 2H), 5.09-5.25 (m, 2H), 5.75-5.95 (m, 1H), 6.65 (d, J=8.7 Hz, 2H), 7.15-7.38 (m, 7H).

後処理

  1. extractionThis solution was extracted three times with dichloromethane (50 mL)
  2. washwashed with sodium carbonate solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto provide a yellow foam
  6. customThis material was purified on a flash silica gel column (5% methanol-chloroform to 10% methanol-chloroform)

出典と根拠

ORDレコード
ord-02398d8c3d644488bbff11ecd28fc1b2
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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