Réaction #75150

ord-de8043b3f6a142a0be495480f4905990

Équation de réaction

CS(=O)(=O)O.O=c1[nH]c2cccc(Cl)c2n1CCCO
4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one methane sulfonate
O=C1NCN(c2ccccc2)C12CCNCC2
1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CC(=O)CC(C)C
4-methyl-2-pentanone
O=C1NCN(c2ccccc2)C12CCN(CCCn1c(=O)[nH]c3cccc(Cl)c31)CC2
8-[3-(7-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one
Rendement 17.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurerefluxed overnight
  2. 2
    TempératureThe reaction mixture is cooled
  3. 3
    FiltrationThe precipitated product is filtered off
  4. 4
    Autrecrystallized twice from a mixture of N,N-dimethylformamide and water

Mode opératoire

A mixture of 4.2 parts of 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one methane sulfonate, 2.5 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one, 10 parts of sodium carbonate and 80 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is cooled and water is added. The precipitated product is filtered off and crystallized twice from a mixture of N,N-dimethylformamide and water, yielding 0.8 parts (17%) of 8-[3-(7-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one; mp. 258.4° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04175129uspto-grants-1979_11