Potassium Iodide → 6-chloro-1{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one 2-propanolate

HRID 1729812ノート

反応式

HRID 1729812 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:6]=2[CH:17]=1.C(=O)([O-])[O-:19].[Na+].[Na+].[I-].[K+].Cl[CH2:27][CH2:28][CH2:29][CH:30]([C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1>O.CC(C)CC(=O)C>[CH3:2][CH:17]([O-:19])[CH3:6].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][N:14]([CH2:27][CH2:28][CH2:29][CH:30]([C:31]4[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=4)[C:38]4[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=4)[CH2:15][CH2:16]3)[C:6]=2[CH:17]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 137921086-Chloro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one

生成物 1

HCID 215002436-chloro-1{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one 2-propanolate

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

A mixture of 5 parts of 6-chloro-1,3-dihydro-1-(4-piperidinyl)- 2H-benzimidazol-2-one, 6.4 parts of sodium carbonate, 0.2 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 30 minutes with water-separator. After cooling for awhile, there are added 7 parts of 1-chloro-4,4-bis(4-fluorophenyl)-butane and stirring at reflux is continued for 20 hours. The reaction mixture is cooled, water is added and the layers are separated. The organic layer is dried, filtered and evaporated. The oily residue is acidified with a diluted hydrochloric acid solution. After shaking thoroughly with toluene, the latter is decanted and discarded. The aqueous acid phase, together with the residual oil, is alkalized with ammonium hydroxide and the product is extracted with toluene. The extract is dried, filtered and evaporated. The oily residue is crystallized from 2-propanol, yielding 6-chloro-1{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one 2-propanolate; mp. 174.6° C.

後処理

  1. temperatureAfter cooling for awhile, there
  2. stirringstirring
  3. temperatureat reflux
  4. temperatureThe reaction mixture is cooled
  5. customthe layers are separated
  6. customThe organic layer is dried
  7. filtrationfiltered
  8. customevaporated
  9. stirringAfter shaking thoroughly with toluene
  10. customthe latter is decanted
  11. extractionthe product is extracted with toluene
  12. customThe extract is dried
  13. filtrationfiltered
  14. customevaporated
  15. customThe oily residue is crystallized from 2-propanol

出典と根拠

ORDレコード
ord-8890f45244ab478197936f0f42196449
出典データセット
uspto-grants-1976_11
特許番号
US03989707

反応ノート

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