Sodium Iodide → 1-[4-Cyano-5-methyl-4-(2-naphthyl)hexyl]-4-[2-(4-fluorophenoxy)ethyl]piperazine

HRID 1071646ノート

反応式

HRID 1071646 の反応式
[C:1]([C:3]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6]O)#[N:2].C(N(CC)CC)C.S(Cl)(C)(=O)=O.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[F:41][C:42]1[CH:56]=[CH:55][C:45]([O:46][CH2:47][CH2:48][N:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[CH:44][CH:43]=1>C(#N)C.[Cl-].[Na+].O.O.CN(C)C=O>[C:1]([C:3]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)([CH:8]([CH3:9])[CH3:10])[CH2:4][CH2:5][CH2:6][N:52]1[CH2:53][CH2:54][N:49]([CH2:48][CH2:47][O:46][C:45]2[CH:44]=[CH:43][C:42]([F:41])=[CH:56][CH:55]=2)[CH2:50][CH2:51]1)#[N:2]

参加物

11

反応物 6

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 8950271-[2-(4-Fluorophenoxy)ethyl]piperazineHCID 223937754-Cyano-5-methyl-4-(2-naphthyl)hexanol

生成物 1

HCID 223936531-[4-Cyano-5-methyl-4-(2-naphthyl)hexyl]-4-[2-(4-fluorophenoxy)ethyl]piperazine収率 69.9%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
60 °C

実験手順

In acetonitrile (5 ml) was dissolved 310 mg (1.16 mmol) of 4-cyano-5-methyl-4-(2-naphthyl)hexanol, followed by adding 190 μL (1.36 mmol) of triethylamine and 105 μl (1.36 mmol) of mesyl chloride. After completion of mesylation, 1.11 g (7.38 mmol) of sodium iodide, 255 mg (1.85 mmol) of potassium carbonate, 414 mg (1.85 mmol) of 1-[2-(4-fluorophenoxy) ethyl]piperazine, 5 ml of dimethylformamide and 1 ml of water were added thereto, followed by heating to 60° C. After completion of the reaction, brine was added thereto and the objective product was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give a crude product. The crude product was subjected to (NH) silica gel (eluted with ethyl acetate/hexane=2/3), to give 384 mg (0.81 mmol, 69.9%) of the title compound as a yellow syrup.

後処理

  1. additionwas added
  2. extractionthe objective product was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customto give a crude product

出典と根拠

ORDレコード
ord-e76a4419ea6b47f2a9c8a9df2889489b
出典データセット
uspto-grants-2005_06
特許番号
US06906072B1

反応ノート

読み込み中…