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Potassium Iodide → 1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-3-(1-methylethyl)-2H-benzimidazol-2-one

HRID 1704524
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HRID 1704524 반응식
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:14]([CH3:16])=[CH2:15])[C:6]1=[O:17].CC([N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[C:22]1=[O:36])C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[O:36]=[C:22]1[N:23]([CH2:30][CH2:31][CH2:32][N:33]2[CH2:34][CH2:35][CH:4]([N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[N:7]([CH:14]([CH3:16])[CH3:15])[C:6]3=[O:17])[CH2:3][CH2:2]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[NH:21]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 30173591-(3-Chloropropyl)-1,3-dihydro-3-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 186959941-(1-methylethyl)-3-(4-piperidinyl)-2H-benzimidazol-2-one

생성물 1

HCID 203855711-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-3-(1-methylethyl)-2H-benzimidazol-2-one수율 64%

시약·촉매·용매 2

HCID 962Water용매HCID 7909Methyl Isobutyl Ketone용매

실험 절차

A mixture of 4.15 parts of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 3.9 parts of 1-(1-methylethyl)-3-(4-piperidinyl)-2H-benzimidazol-2-one, 3.2 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is cooled to room temperature, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol. The solvent is evaporated and the residue is suspended in water. The suspension is alkalized with a diluted ammonium hydroxide solution and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 4.2 parts (64%) of 1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-3-(1-methylethyl)-2H-benzimidazol-2-one; mp. 174.3° C.

후처리

  1. temperaturerefluxed overnight
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. stirringThe residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol
  7. customThe solvent is evaporated
  8. extractionthe product is extracted with trichloromethane
  9. customThe extract is dried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is purified by column-chromatography over silica gel using
  13. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  14. customThe pure fractions are collected
  15. customthe eluent is evaporated
  16. customThe residue is crystallized from 4-methyl-2-pentanone
  17. filtrationThe product is filtered off
  18. customdried

출처 및 근거

ORD 기록
ord-daa013e6181c4023a054b1c2abe504bf
출처 데이터셋
uspto-grants-1978_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04126687

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