Ethylenediamine → 2-(4-Methoxyphenyl)piperazine

HRID 1784656노트

반응식

HRID 1784656 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 27717532-(4-Methoxyphenyl)piperazine수율 45.3%

시약·촉매·용매 2

HCID 887Methanol용매3회HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-1bb930f324334d69b46eb823f018c576
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504411B2

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