StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium Carbonate → 3-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-N-(2,4,6-trimethyl-3-pyridinyl)-1-piperazineacetamide trihydrochloride

HRID 1494655
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1494655
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]2[C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1.[ClH:29].[Cl:30][CH2:31][C:32]([NH:34][C:35]1[C:36]([CH3:43])=[N:37][C:38]([CH3:42])=[CH:39][C:40]=1[CH3:41])=[O:33].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[ClH:30].[ClH:29].[ClH:30].[NH2:21][C:19]([CH:14]1[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH:8]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:18][CH2:17][N:16]([CH2:31][C:32]([NH:34][C:35]2[C:36]([CH3:43])=[N:37][C:38]([CH3:42])=[CH:39][C:40]=2[CH3:41])=[O:33])[CH2:15]1)=[O:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 150877291-[5,5-Bis(4-fluorophenyl)pentyl]-2-piperazinecarboxamideHCID 198284682-chloro-N-(2,4,6-trimethyl-3-pyridinyl)acetamide monohydrochloride

Produkt 1

HCID 867448813-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-N-(2,4,6-trimethyl-3-pyridinyl)-1-piperazineacetamide trihydrochlorideAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 6.1 parts of 1-[5,5-bis(4-fluorophenyl)pentyl]-2-piperazinecarboxamide, 4.3 parts of 2-chloro-N-(2,4,6-trimethyl-3-pyridinyl)acetamide monohydrochloride, 3.7 parts of sodium carbonate and 90 parts of N,N-dimethylformamide was stirred for 15 hours at 70° C. The reaction mixture was filtered, washed with N,N-dimethylformamide and the filtrate was evaporated in vacuo. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (92.5:7.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was further 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 converted into the hydrochloride salt in 2-propanone and 2-propanol. The salt was filtered off, washed twice with 2-propanone and once with 2,2'-oxybispropane and dried overnight at 100°-110° C., yielding 6.58 parts (61.2%) of 3 -(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-N-(2,4,6-trimethyl-3-pyridinyl)-1-piperazineacetamide trihydrochloride, hemihydrate; mp. 224.7° C. (compound 115).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washwashed with N,N-dimethylformamide
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (92.5:7.5 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was further purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe salt was filtered off
  13. washwashed twice with 2-propanone and once with 2,2'-oxybispropane
  14. customdried overnight at 100°-110° C.

Quellen und Nachweise

ORD-Eintrag
ord-f874b8c716e64c1c80d106ad1ba3a556
Quelldatensatz
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05026853

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion