1,1'-Carbonyldiimidazole → Pruvanserin

HRID 971072

Reaktionsgleichung

Reaktionsgleichung von HRID 971072
[C:1]([C:3]1[C:11]2[C:6](=[C:7]([C:12]([OH:14])=O)[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[CH:32][CH:31]=1>CN1CCCC1=O>[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][N:38]2[CH2:39][CH2:40][N:41]([C:12]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:6]=3[NH:5][CH:4]=[C:3]4[C:1]#[N:2])=[O:14])[CH2:42][CH2:43]2)=[CH:32][CH:31]=1

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 113674313-Cyano-1H-indole-7-carboxylic acidHCID 451583331-[2-(4-Fluorophenyl)ethyl]piperazine dihydrochloride

Produkt 1

HCID 6433122Pruvanserin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

5 g (0.027 mol) of 3-cyanoindole-7-carboxylic acid are dissolved in 40 ml of hot N-methylpyrrolidone, the solution is cooled to 40°, and 7.6 g (0.027 mol) of N,N-carbonyldiimidazole are added. The mixture is stirred at room temperature for a further one hour. A suspension of 1-(2-(4-fluorophenyl)ethyl)piperazine dihydrochloride in 40 ml of N-methylpyrrolidone is subsequently poured in. After 5 minutes, a clear solution is formed and just afterwards white crystals deposit. The mixture is stirred overnight at room temperature. The crystals are filtered off with suction, washed and dried, giving 5 g of 7-{4-[2-(4-fluorophenyl)ethyl]piperazin-1-carbonyl}-1H-indole-3-carbonitrile as the free base having a melting point (m.p.) of 192.0-193.5°.

Aufarbeitung

  1. temperaturethe solution is cooled to 40°
  2. additionis subsequently poured in
  3. waitAfter 5 minutes
  4. customa clear solution is formed
  5. stirringThe mixture is stirred overnight at room temperature
  6. filtrationThe crystals are filtered off with suction
  7. washwashed
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2164d0cef5b9403696677fdf3ab962de
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312342B2

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