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

HRID 35340

Reaktionsgleichung

Reaktionsgleichung von HRID 35340
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 14230222N-(2,6-dimethylphenyl)-2-(1-hydroxyethyl)-4-(phenylmethyl)-1-piperazineacetamideAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-75fdca07dd8d42d88dc2c02046d78d62
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766125

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