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 979933ノート

反応式

HRID 979933 の反応式
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

参加物

7

反応物 4

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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c4cd608fbc59417dbc9f07e033b48523
出典データセット
uspto-grants-1987_01
特許番号
US04634704

反応ノート

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