p-Toluenesulfonic acid → ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]hexahydro-1H-azepine-1-carboxylate

HRID 1460524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1460524
O=[C:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=[C:23]2[NH2:31])=[CH:17][CH:16]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>CO.O.C(O)C.CC1C=CC=CC=1>[F:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=[C:23]2[NH:31][CH:2]2[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]2)=[CH:19][CH:20]=1

Komponenten

9

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 30193052-amino-1-((4-fluorophenyl)methyl)-1H-benzimidazoleHCID 4311764Sodium borohydrideHCID 126660861-Carbethoxyazepan-4-one

Produkt 1

HCID 15037357ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]hexahydro-1H-azepine-1-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 33.3 parts of ethyl hexahydro-4-oxo-1H-azepine-1-carboxylate, 36.15 parts of 1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine, 320 parts of methylbenzene and 0.1 parts of 4-methylbenzenesulfonic acid was stirred overnight at reflux temperature using a water separator. After cooling to 50° C., 80 parts of ethanol were added. 4.2 Parts of sodium tetrahydroborate were added portionwise and upon completion, stirring was continued for 2 hours at 50° C. After cooling, water and 4.8 parts of methanol were added while stirring. The layers were separated and the aqueous layer was extracted with methylbenzene. The combined organic layers were dried, filtered and evaporated, yielding 73 parts (100%) of ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]hexahydro-1H-azepine-1-carboxylate as a residue (compound 20).

Aufarbeitung

  1. temperatureat reflux temperature
  2. stirringstirring
  3. waitwas continued for 2 hours at 50° C
  4. temperatureAfter cooling
  5. stirringwhile stirring
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with methylbenzene
  8. customThe combined organic layers were dried
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ba9a283a693740749fc49251fbc2d64b
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05071846

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