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Methyl Isobutyl Ketone → 2-[[1-[3-(4-fluorophenoxy)propyl]-4-piperidinyl]methyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazole ethanedioate

HRID 2309633
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HRID 2309633 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[C:25](=[O:28])([O-:27])[O-].[Na+].[Na+].CC(C)C[C:34](=[O:36])C.Cl[CH2:39][CH2:40][CH2:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=1>O>[C:34]([OH:36])(=[O:42])[C:25]([OH:27])=[O:28].[F:49][C:46]1[CH:47]=[CH:48][C:43]([O:42][CH2:41][CH2:40][CH2:39][N:22]2[CH2:21][CH2:20][CH:19]([CH2:18][C:10]3[N:9]([CH2:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[N:11]=3)[CH2:24][CH2:23]2)=[CH:44][CH:45]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 743911-(3-Chloropropoxy)-4-fluorobenzeneHCID 140128661-[(4-fluorophenyl)methyl]-2-(4-piperidinylmethyl)-1H-benzimidazole

생성물 1

HCID 1317152632-[[1-[3-(4-fluorophenoxy)propyl]-4-piperidinyl]methyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazole ethanedioate수율 53%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A mixture of 6.5 parts of 1-[(4-fluorophenyl)methyl]-2-(4-piperidinylmethyl)-1H-benzimidazole, 4.2 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 30 minutes using a water separator. 5.2 Parts of 1-(3-chloropropoxy)-4-fluorobenzene were added at reflux temperature and stirring was continued for 3 hours at this temperature using a water separator. After cooling to room temperature, the salts were filtered off and the filtrate was washed twice with water, dried, filtered and evaporated. The residue was converted into the ethanedioate salt in 2-propanone. The salt was filtered off, washed with 2-propanone and crystallized from methanol. The product was filtered off and dried in vacuo at 80° C., yielding 7 parts (53%) of 2-[[1-[3-(4-fluorophenoxy)propyl]-4-piperidinyl]methyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazole ethanedioate (1:2); mp. 186.7° C. (119).

후처리

  1. temperaturerefluxed for 30 minutes
  2. temperatureat reflux temperature
  3. stirringstirring
  4. filtrationthe salts were filtered off
  5. washthe filtrate was washed twice with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe salt was filtered off
  10. washwashed with 2-propanone
  11. customcrystallized from methanol
  12. filtrationThe product was filtered off
  13. customdried in vacuo at 80° C.

출처 및 근거

ORD 기록
ord-ee2e4e81a8ea4292b2fc6d084f27a2c0
출처 데이터셋
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04695575

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