Toluene → 3-acetyl-5-chloro-1-{1-[3-(3-acetyl-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one

HRID 1704526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1704526
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32].C[C:39]1[CH:44]=CC=CC=1.C(=O)([O-])[O-:46].[Na+].[Na+]>O>[C:31]([N:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:30]=[CH:29][C:5]=2[N:6]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([C:44](=[O:46])[CH3:39])[C:20]3=[O:28])[CH2:12][CH2:11]2)[C:7]1=[O:9])(=[O:33])[CH3:32]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 3151DomperidoneHCID 7918Acetic AnhydrideHCID 10340Sodium Carbonate

Produkt 1

HCID 203856083-acetyl-5-chloro-1-{1-[3-(3-acetyl-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5 parts of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one, 10 parts of acetic acid anhydride and 90 parts of methylbenzene is stirred and refluxed overnight. The reaction mixture is cooled, water is added and the whole is alkalized with a diluted sodium carbonate solution. The layers are separated and the organic phase is dried, filtered and evaporated. The residue is crystallized from methylbenzene. The product is filtered off and recrystallized from methylbenzene, yielding 4.5 parts of 3-acetyl-5-chloro-1-{1-[3-(3-acetyl-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 185.3° C.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customThe layers are separated
  4. customthe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from methylbenzene
  8. filtrationThe product is filtered off
  9. customrecrystallized from methylbenzene

Quellen und Nachweise

ORD-Eintrag
ord-f2f77b7f58954b94a84de936db015d6d
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04126687

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