Potassium Iodide → 2H-Benzimidazol-2-one, 1,3-dihydro-1-(1-(4,4-bis(4-fluorophenyl)cyclohexyl)-4-piperidinyl)-5-chloro-

HRID 616992노트

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HRID 616992 반응식
S(C1C=CC(C)=CC=1)(O[CH:5]1[CH2:10][CH2:9][C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=O)=O.[NH:32]1[CH2:37][CH2:36][CH:35]([N:38]2[C:42]3[CH:43]=[CH:44][C:45]([Cl:47])=[CH:46][C:41]=3[NH:40][C:39]2=[O:48])[CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CCOCC.O.CN(C)C=O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:7][CH2:6][CH:5]([N:32]3[CH2:33][CH2:34][CH:35]([N:38]4[C:42]5[CH:43]=[CH:44][C:45]([Cl:47])=[CH:46][C:41]=5[NH:40][C:39]4=[O:48])[CH2:36][CH2:37]3)[CH2:10][CH2:9]2)=[CH:12][CH:13]=1

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 20366914HCID 20366914, 화합물

생성물 1

HCID 30459002H-Benzimidazol-2-one, 1,3-dihydro-1-(1-(4,4-bis(4-fluorophenyl)cyclohexyl)-4-piperidinyl)-5-chloro-

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 11 g of 4,4-bis(p-fluorophenyl)cyclohexyl tosylate, 6 g of 1-(4-piperidyl)-5-chloro-2-benzimidazolinone, 3.5 g of potassium carbonate, 4.1 g of potassium iodide and 80 ml of dimethylformamide is stirred at 70°-80° C for 64 hours. The reaction mixture is poured into water, ether is added to the separated semi-solid, and the whole is stirred for 30 minutes. The substance insoluble in water and ether is collected by filtration, washed with ether and dried. The obtained crystals are dissolved in a mixture of chloroform and methanol (9:1), and the solution is concentrated to some degree and cooled. The precipitated crystals are collected by filtration and purified in the same manner to give 1-[1-(4,4-bis(p-fluorophenyl)cyclohexyl)-4-piperidyl]-5-chloro-2-benzimidazolinone as white crystals, melting at 279°-284° C.

후처리

  1. additionis added to the separated semi-solid
  2. stirringthe whole is stirred for 30 minutes
  3. filtrationThe substance insoluble in water and ether is collected by filtration
  4. washwashed with ether
  5. customdried
  6. dissolutionThe obtained crystals are dissolved in a mixture of chloroform and methanol (9:1)
  7. concentrationthe solution is concentrated to some degree
  8. temperaturecooled
  9. filtrationThe precipitated crystals are collected by filtration
  10. custompurified in the same manner

출처 및 근거

ORD 기록
ord-30367c1dca2c45798308895eb59e9ad0
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04076821

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