Potassium Iodide → Declenperone

HRID 258852ノート

反応式

HRID 258852 の反応式
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7](C(C)=C)[C:6]1=[O:17].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)CC(=O)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([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:17])[CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:24]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 30173591-(3-Chloropropyl)-1,3-dihydro-3-(1-methylvinyl)-2H-benzimidazol-2-one

生成物 1

HCID 71744Declenperone収率 20%

試薬・触媒・溶媒 1

HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

A mixture of 5 parts of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 4.5 parts of (4-fluorophenyl) (4-piperidinyl) methanone, 10 parts of sodium carbonate, 0.2 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. After cooling, the reaction mixture is poured onto water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is taken up in 2-propanone and 2-propanol, previously saturated with gaseous hydrogen chloride, is added. After boiling for 30 minutes, the mixture is evaporated. A diluted hydrochloric acid solution is added to the residue and the whole is stirred and warmed at 40°-45° C for 1 hour. After the addition of 4-methyl-2-pentanone, the mixture is alkalized with ammonium hydroxide and the layers are separated. The organic phase is dried, filtered and and evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 1.5 parts (20%) of 1-{3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 163.9° C.

後処理

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. additionthe reaction mixture is poured onto water
  4. customthe layers are separated
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated
  8. addition2-propanol, previously saturated with gaseous hydrogen chloride, is added
  9. customthe mixture is evaporated
  10. additionA diluted hydrochloric acid solution is added to the residue
  11. stirringthe whole is stirred
  12. temperaturewarmed at 40°-45° C for 1 hour
  13. additionAfter the addition of 4-methyl-2-pentanone
  14. customthe layers are separated
  15. customThe organic phase is dried
  16. filtrationfiltered
  17. customevaporated
  18. customThe residue is crystallized from 4-methyl-2-pentanone
  19. filtrationThe product is filtered off
  20. customdried

出典と根拠

ORDレコード
ord-83c6375fac394998adf017bd4fab69af
出典データセット
uspto-grants-1977_07
特許番号
US04035369

反応ノート

読み込み中…