Potassium Iodide → 1-[(4-fluorophenyl)methyl]-N-[1'-[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-[1,4'-bipiperidin]-4-yl]-1H-benzimidazol-2-amine monohydrate

HRID 979933노트

반응식

HRID 979933 반응식
Cl[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[N:29]=[C:28]2[NH:36][CH:37]2[CH2:42][CH2:41][N:40]([CH:43]3[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]3)[CH2:39][CH2:38]2)=[CH:22][CH:21]=1.[I-].[K+].C(=O)([O-])[O-:52].[K+].[K+]>O.ClC(Cl)Cl>[OH2:52].[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][N:27]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[N:29]=[C:28]2[NH:36][CH:37]2[CH2:42][CH2:41][N:40]([CH:43]3[CH2:48][CH2:47][N:46]([C:2]4[N:6]([CH2:7][C:8]5[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=5)[C:5]5[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=5[N:3]=4)[CH2:45][CH2:44]3)[CH2:39][CH2:38]2)=[CH:24][CH:25]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 30202411-(4-Fluorobenzyl)-2-chlorobenzimidazoleHCID 15614720N-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl][1,4'-bipiperidine]-4-amine

생성물 1

HCID 202228991-[(4-fluorophenyl)methyl]-N-[1'-[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-[1,4'-bipiperidin]-4-yl]-1H-benzimidazol-2-amine monohydrate

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

반응 조건

온도
130 °C

실험 절차

A mixture of 4 parts of 2-chloro-1-[(4-fluorophenyl)methyl]-1H-benzimidazole, 6.1 parts of N-[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-[1,4'-bipiperidine]-4-amine and 1 part of potassium iodide was stirred and heated for 3 hours at 130° C. The reaction mixture was cooled and taken up in water and trichloromethane. The whole was alkalized with potassium carbonate. The organic phase was separated, dried, filtered and evaporated. The residue was purified by HPLC using a mixture of trichloromethane and methanol (98:2 by volume), saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 1.6 parts of 1-[(4-fluorophenyl)methyl]-N-[1'-[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-[1,4'-bipiperidin]-4-yl]-1H-benzimidazol-2-amine monohydrate; mp. 130.2° C. (compound 65).

후처리

  1. temperatureThe reaction mixture was cooled
  2. customThe organic phase was separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by HPLC
  7. additiona mixture of trichloromethane and methanol (98:2 by volume)
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from acetonitrile

출처 및 근거

ORD 기록
ord-c4cd608fbc59417dbc9f07e033b48523
출처 데이터셋
uspto-grants-1987_01
특허 번호
US04634704

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