Ethylenediamine → 2-(4-Methoxyphenyl)piperazine

HRID 1784656ノート

反応式

HRID 1784656 の反応式
[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH:15]=O)=O)=[CH:9][CH:8]=1.[BH4-].[Na+]>CO.O1CCCC1>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:15][NH:4][CH2:1][CH2:2][NH:3]2)=[CH:9][CH:8]=1

参加物

6

反応物 3

HCID 3301EthylenediamineHCID 70643(4-Methoxyphenyl)glyoxalHCID 4311764Sodium borohydride

生成物 1

HCID 27717532-(4-Methoxyphenyl)piperazine収率 45.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒3 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Methanol (5 ml) solution of ethylenediamine (3.74 g, 62.29 mmol) was added to the ice-cooled solution of 4-methoxyphenylglyoxal (8.30 g, 45.5 mmol) in methanol (100 ml) and tetrahydrofuran (50 ml) and stirred for 10 min. After cooling to 0° C., sodium tetrahydroborate (6.14 g, 162.2 mmol) and additional methanol (50 ml) was added and stirred overnight. After removal of the solvent, aqueous sodium hydroxide was added and was extracted with dichloromethane three times and washed with brine and dried over sodium sulfate. After removal of the solvent, purification of the residue by silica gel column chromatography (eluent; dichloromethane/ethanol/diethylamine=20/2/1) gave 2-(4-methoxypheny)-piperazine (3.96 g, 45%).

後処理

  1. stirringstirred overnight
  2. customAfter removal of the solvent, aqueous sodium hydroxide
  3. additionwas added
  4. extractionwas extracted with dichloromethane three times
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removal of the solvent, purification of the residue by silica gel column chromatography (eluent; dichloromethane/ethanol/diethylamine=20/2/1)

出典と根拠

ORDレコード
ord-1bb930f324334d69b46eb823f018c576
出典データセット
uspto-grants-2009_03
特許番号
US07504411B2

反応ノート

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