Potassium Iodide → N-(2,6-dimethylphenyl)-2-(1-hydroxyethyl)-4-(phenylmethyl)-1-piperazineacetamide

HRID 35340

반응식

HRID 35340 반응식
[CH3:1][CH:2]([CH:4]1[CH2:9][N:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6][NH:5]1)[OH:3].Cl[CH2:18][C:19]([NH:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:29])=[O:20].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[CH3:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:29])[C:22]=1[NH:21][C:19](=[O:20])[CH2:18][N:5]1[CH2:6][CH2:7][N:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH:4]1[CH:2]([OH:3])[CH3:1]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamideHCID 14230267alpha-Methyl-4-(phenylmethyl)-2-piperazinemethanol

생성물 1

HCID 14230222N-(2,6-dimethylphenyl)-2-(1-hydroxyethyl)-4-(phenylmethyl)-1-piperazineacetamide수율 84.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of 24.0 parts of α-methyl-4-(phenylmethyl)-2-piperazinemethanol, 27.3 parts of 2-chloro-N-(2,6-dimethylphenyl)acetamide, 25.4 parts of sodium carbonate, 0.1 parts of potassium iodide and 180 parts of N,N-dimethylformamide was stirred for 18 hours at 60° C. The reaction mixture was poured onto water and the product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 1,1'-oxybisethane, yielding 35.19 parts (84.8%) of N-(2,6-dimethylphenyl)-2-(1-hydroxyethyl)-4-(phenylmethyl)-1-piperazineacetamide; mp. 148.8° C. (compound 113).

후처리

  1. additionThe reaction mixture was poured onto water
  2. extractionthe product was extracted with dichloromethane
  3. washThe extract was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 1,1'-oxybisethane

출처 및 근거

ORD 기록
ord-75fdca07dd8d42d88dc2c02046d78d62
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766125

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