Potassium Iodide → HCID 131716780, Verbindung

HRID 981314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 981314
[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Br[CH:31]([CH3:51])[CH2:32][C:33]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:34]([N:36]([CH3:38])[CH3:37])=[O:35]>O.CC(C)CC(=O)C>[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH:31]([CH3:51])[CH2:32][C:33]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:34]([N:36]([CH3:37])[CH3:38])=[O:35])[CH2:11][C@H:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 98616214-Amino-5-chloro-2-methoxy-N-[(3R,4S)-3-methoxypiperidin-4-YL]benzamideHCID 20071680HCID 20071680, Verbindung

Produkt 1

HCID 131716780HCID 131716780, VerbindungAusbeute 31,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

4.71 parts of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide, 3.66 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 15 minutes using a water separator. 6 parts of α-(2-bromopropyl)-N,N-dimethyl-α-phenylbenzeneacetamide were added and stirring was continued for 2.5 hours at reflux. Water was added. The organic layer was separated, washed with a sodium chloride solution, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and crystallized from acetonitrile, yielding 2.83 parts (31.8%) of cis-4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-3-methoxy-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide; mp. 198.3° C. (compound 54).

Aufarbeitung

  1. temperaturerefluxed for 15 minutes
  2. temperatureat reflux
  3. customThe organic layer was separated
  4. washwashed with a sodium chloride solution
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe product was filtered off
  13. customcrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-a8a69f9422ff49d987c092218e1a0606
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990521

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