Methyl Isobutyl Ketone → 3-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2,6-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 66680

Reaktionsgleichung

Reaktionsgleichung von HRID 66680
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:7]2=[N:6][C:5]=1[CH3:16].[NH:17]1[CH2:22][CH2:21][CH:20]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[NH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([CH:20]2[CH2:21][CH2:22][N:17]([CH2:2][CH2:3][C:4]3[C:9](=[O:10])[N:8]4[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:7]4=[N:6][C:5]=3[CH3:16])[CH2:18][CH2:19]2)=[CH:24]1

Komponenten

6

Edukt 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 46254083-(2-chloroethyl)-2,6-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one

Produkt 1

HCID 205307303-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2,6-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-oneAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 4.8 parts of 3-(2-chloroethyl)-2,6-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one, 4 parts of 3-(4-piperidinyl)-1H-indole, 8.5 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight using a water-separator. The reaction mixture is cooled, water is added and the precipitated product is filtered off. It is dissolved in a mixture of trichloromethane and methanol (90:10 by volume). The solution is filtered over silica gel and the filtrate is evaporated. The residue is crystallized from 2-propanol, yielding 2.5 parts (31%) of 3-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2,6-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 224.9° C.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. filtrationthe precipitated product is filtered off
  4. dissolutionIt is dissolved in a mixture of trichloromethane and methanol (90:10 by volume)
  5. filtrationThe solution is filtered over silica gel
  6. customthe filtrate is evaporated
  7. customThe residue is crystallized from 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-836d77623d8249978e224193b04e3783
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04342870

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