Sodium Carbonate → 1-[3-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]propyl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 126871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 126871
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[NH:7][C:6]3=[O:14])[CH2:27][CH2:26]2)=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 20288069HCID 20288069, Verbindung

Produkt 1

HCID 202880661-[3-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]propyl]-1,3-dihydro-2H-benzimidazol-2-oneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2.3 parts of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one, 2.57 parts of 1-(4-fluorophenyl)-2-(4-piperidinyl)ethanone hydrochloride, 2.65 parts of sodium carbonate and 22.5 parts of N,N-dimethylformamide is stirred for 4 hours at 70°-80° C. The reaction mixture is poured onto water and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and recrystallized from 2-propanol, yielding 1.4 parts (35%) of 1-[3-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]propyl]-1,3-dihydro-2H-benzimidazol-2-one; mp. 208° C.

Aufarbeitung

  1. additionThe reaction mixture is poured onto water
  2. extractionthe product is extracted with trichloromethane
  3. customThe extract is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is crystallized from 4-methyl-2-pentanone
  7. filtrationThe product is filtered off
  8. customrecrystallized from 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-cf0b949d06684ee5853d505427e29387
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254127

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